Dimethylformamide → 2-Amino-1-nitro-4-(2-benzyloxyethoxy)benzene

HRID 596579Notes

Reaction equation

HRID 596579 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[H-].[Na+].[NH2:19][C:20]1[CH:25]=[C:24](Cl)[CH:23]=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28]>O>[NH2:19][C:20]1[CH:25]=[C:24]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:23]=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 121412-(Benzyloxy) ethanolHCID 24758Sodium hydrideHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 214502112-Amino-1-nitro-4-(2-benzyloxyethoxy)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7.5 g. of 2-benzyloxyethanol in 30 ml. of dimethylformamide is treated with 1.2 g. of sodium hydride. When the mixture is homogeneous, 3.5 g. of 2-amino-4-chloro-1-nitrobenzene is added and the mixture heated at 110°-120° for 4 hours. The mixture is cooled, diluted with water and extracted with benzene. The crude product is treated with charcoal and isolated by precipitation with cyclohexane to afford 2-amino-1-nitro-4-(2-benzyloxyethoxy)benzene.

Workup

  1. temperaturethe mixture heated at 110°-120° for 4 hours
  2. temperatureThe mixture is cooled
  3. extractionextracted with benzene
  4. additionThe crude product is treated with charcoal
  5. customisolated by precipitation with cyclohexane

Sources & evidence

ORD record
ord-ae1da035c4cc4daba206eba848489b8b
Source dataset
uspto-grants-1977_03
Patent number
US04011320

Reaction notes

Loading…