Methanol → 4-[2-(Benzyloxy)ethoxy]benzene-1,2-diamine

HRID 1730818Notes

Reaction equation

HRID 1730818 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:4][C:3]=1[N+:19]([O-])=O.CO.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:19][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH2:10][O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 24489Sodium DithioniteHCID 214502112-Amino-1-nitro-4-(2-benzyloxyethoxy)benzene

Product 1

HCID 214502064-[2-(Benzyloxy)ethoxy]benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.6 G. of 2-amino-4-(2-benzyloxyethoxy)-1-nitrobenzene is treated in 100 ml. of methanol and 50 ml. of water with 10 g. of sodium hydrosulfite (Na2S2O4) on the steam bath for 15 minutes. The reaction mixture is concentrated under vacuum and extracted with chloroform. Evaporationn of the extract affords 1,2-diamino-4-(2-benzyloxyethoxy)benzene.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. extractionextracted with chloroform

Sources & evidence

ORD record
ord-406a628b08424dfeb74bd2e47771a6a4
Source dataset
uspto-grants-1976_11
Patent number
US03993768

Reaction notes

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