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Substances (2)
Citations (5)
Conditions
References
1
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5.4 g (91%)
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Rx-ID: 9385449 Find similar reactions
With nitrating agent in water
Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo
British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details
With conc. HNO3 in hydrochlorid acid; sodium hydroxide; water
Roche Diagnostics Corporation
Patent: US6525200 B1, 2003 ;
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5.A:A. A. Synthesis of Intermediate 33-(2,5-Dimethoxy-4-nitrophenethylamine) To a 100-mL Erlenmeyer flask equipped with a magnetic stirring bar were added 4.73 g (26.1 mmol) of 2,5-dimethoxyphenethylamine (32) (Trans World Chemicals Inc., 98percent) and 4.2 mL of water. The mixture was stirred and cooled to 0° C. in an ice bath and 3.1 mL of conc. HCl was added slowly. To the resulting yellow solution 3.4 mL of conc. HNO3 was added dropwise at 0-5° C. over a period of 1 h. Then 12 mL of water was added to the solidified mixture and swirled to form a stirrable paste. Then another 3.4 mL of conc. HNO3 was added dropwise at 0-5° C. over a period of 1 h.
The yellow mixture was refrigerated for 12 h., then 20 mL of water was added and ultrasonicated to brake big chunks of solid. The suspension was cooled to 0° C. in an ice bath and 10 mL of 40percent NaOH was added slowly to achieve pH 12-13. The mixture was extracted with CHCl3 (3*10 mL) and the combined extract was washed with 0.5 N NaOH (3*10 mL), dried over K2CO3 (3 g) and evaporated to dryness (15 mm) to give 5.4 g (91percent) of 33 as a brown oil which solidified after 0.5 h at room temperature. 1H NMR (300 MHz, CDCl3): δ7.43 (s, 1H, H3), 6.96 (s, 1H, H6), 3.95 (s, 3H, H10), 3.85 (s, 3H, H9), 3.00 (t, J=6.9 Hz, 2H, H8), 2.85 (t, J=6.9 Hz, 2H, H7), 2.06 (s, 2H, NH2); 13C NMR (75.7 MHz, CDCl3): δ150.6, 147.3, 136.8, 136.5, 116.2, 107.2, 56.9, 55.8, 41.6, 34.9. FAB-MS, m/z (rel. intensity):
227.3 (M+1, 100). For microanalysis crude 33was recrystallized from a 1:5 mixture of EtOAc/hexane and dried under vacuum (0.1 mm, RT) for 2 days; mp 64-66° C. Anal. Calcd for C10H14N2O4: C, 53.09; H, 6.23; N, 12.38percent. Found: C, 53.04; H, 6.03; N, 12.30percent. With sodium hydroxide in water; acetic acid; benzene
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Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip
Patent: US2015/38366 A1, 2015 ; Location in patent: Page/Page column ; Title/Abstract Full Text Show Details
3:Preparation of 2-(2,5-dimethoxy-4-nitrophenyl)ethanamine 4
Example 3 Preparation of 2-(2,5-dimethoxy-4-nitrophenyl)ethanamine 4 2-(2,5-Dimethoxyphenyl) ethanamine 3 (5.76 g, 31.78 mmol) was dissolved in a mixture of acetic acid (115 ml) and nitric acid (19 ml) with cooling at 0° C. The reaction mixture was stirred for 1 hour at 0° C. The reaction mixture was poured over a mixture of water and ice and 6M sodium hydroxide was used to bring the pH to alkaline. Then the solution was extracted with a mixture of (1/1) benzene/ether. The organic layer was dried over sodium sulfate, filtered and was evaporated to dryness to give 6.16 g of 2-(2,5-dimethoxy-4-nitrophenyl) ethanamine 4 as dark brown crude oil used in the next step without any further purification.
With sodium hydroxide in water; acetic acid; benzene
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Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip
Patent: EP2835648 A1, 2015 ; Location in patent: Page/Page column ; Title/Abstract Full Text Show Details
3:Example 3
Example 3 Preparation of 2-(2,5-dimethoxy-4-nitrophenyl)ethanamine 4 2-(2,5-Dimethoxyphenyl) ethanamine 3 (5.76g, 31.78mmol) was dissolved in a mixture of acetic acid (115ml) and nitric acid (19ml) with cooling at 0°C. The reaction mixture was stirred for 1 hour at 0°C. The reaction mixture was poured over a mixture of water and ice and 6M sodium hydroxide was used to bring the pH to alkaline. Then the solution was extracted with a mixture of (1/1) benzene/ether. The organic layer was dried over sodium sulfate, filtered and was evaporated to dryness to give 6.16g of 2-(2,5-dimethoxy-4-nitrophenyl) ethanamine 4 as dark brown crude oil used in the next step without any further purification. With nitric acid in acetic acid
T=0°C; 1 h; Hide Experimental Procedure
Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan
Patent: EP2950104 A1, 2015 ; Location in patent: Paragraph 0012; 0066 ; Title/Abstract Full Text Show Details
3:Example 3
Example 3 Preparation 2-(2, 5-dimethoxy-4-nitrophenyl)ethylamine 4 To a cooled solution of 2-(2, 5-dimethoxyphenyl)ethylamine 3 (12.0 g, 0.066 mol) in acetic acid (200 ml) was added nitric acid (40 ml) and the solution was stirred at 0 °C for 1 hour. The mixture was poured into a mixture of ice and water. The mixture was then made strongly alkaline with 6 M NaOH. The basic solution was extracted with a mixture of benzene/ether (1/1) (2x 200 ml). The organic layers were washed by water (100 ml) and brine (100 ml), dried over Na2SO4 and filtered. The filtrate was concentrated to dryness under vacuum to give 11.2 g of 2-(2, 5-dimethoxy-4-nitrophenyl)ethanamine 4 as a brown dark oil (crude) used in the next step without any further purification.
2
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3
Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip
Patent: US2015/38366 A1, 2015 ;
Multi-step reaction with 3 steps 1: ammonium acetate / 20 °C / |Reflux 2: lithium aluminium tetrahydride; sodium hydroxide / tetrahydrofuran / 4.75 h / |Reflux 3: nitric acid / acetic acid / 1 h / 0 °C View Scheme
Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan
Patent: EP2950104 A1, 2015 ;
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Title/Abstract Full Text Show Details
Multi-step reaction with 2 steps 1: sodium hydroxide / tetrahydrofuran; water 2: sodium hydroxide / water; acetic acid; benzene View Scheme
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Rx-ID: 39269974 Find similar reactions
Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip
Patent: US2015/38366 A1, 2015 ; Title/Abstract Full Text Show Details
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Rx-ID: 39269963 Find similar reactions
Multi-step reaction with 3 steps 1: ammonium acetate / nitromethane; dichloromethane; hexane 2: sodium hydroxide / tetrahydrofuran; water 3: sodium hydroxide / water; acetic acid; benzene View Scheme
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4
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Multi-step reaction with 2 steps 1: sodium hydroxide / tetrahydrofuran; water
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Rx-ID: 39318743 Find similar reactions
Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip
2: sodium hydroxide / water; acetic acid; benzene View Scheme
Patent: EP2835648 A1, 2015 ;
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride; sodium hydroxide / tetrahydrofuran / 4.75 h / |Reflux 2: nitric acid / acetic acid / 1 h / 0 °C View Scheme
Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan
Patent: EP2950104 A1, 2015 ;
Title/Abstract Full Text Show Details
Title/Abstract Full Text Show Details