2-Nitroaniline → N-(4-methoxybutyl)-2-nitroaniline
Reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[Br-].[K+].Cl[CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH3:19].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:19][O:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2]Participants
Conditions
- Temperature
- 90 °C
Procedure
Toluene (500 mL) was added to o-nitroaniline (50.0 g, 0.362 mol), tetrabutylammonium bromide (58.3 g, 0.181 mol) and potassium bromide (43.1 g, 0.362 mol). 1-Chloro-4-methoxybutane (66.6 g, 0.543 mol) and 50 w/v % aqueous sodium hydroxide solution (145 mL, 1.81 mol) were added at 20-30° C. The reaction mixture was heated to 85-95° C., and stirred for 6 hr. After allowing to cool to 20-30° C., the reaction mixture was washed successively with water (250 mL), 1N hydrochloric acid (250 mL×2), 5 w/v % sodium bicarbonate water (250 mL) and water (250 mL). The organic layer was concentrated under reduced pressure to the content (250 mL), and toluene (100 mL) was added to give a toluene solution (350 mL) of N-(4-methoxybutyl)-2-nitroaniline (yield 100%).
Workup
- temperatureto cool to 20-30° C.
- washthe reaction mixture was washed successively with water (250 mL), 1N hydrochloric acid (250 mL×2), 5 w/v % sodium bicarbonate water (250 mL) and water (250 mL)
- concentrationThe organic layer was concentrated under reduced pressure to the content (250 mL), and toluene (100 mL)
- additionwas added
Sources & evidence
- ORD record
- ord-a65f026791714c46b67632f1f598236d
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018374B2
Reaction notes
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