Methanol → 4-(2-Methoxyethoxy)benzene-1,2-diamine

HRID 1679461Notes

Reaction equation

HRID 1679461 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:7][C:5]=1[NH2:6])([O-])=O.CO.C(=O)([O-])[O-].[Na+].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:1][C:4]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:7][C:5]=1[NH2:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 222269815-(2-Methoxyethoxy)-2-nitroaniline

Product 1

HCID 542493234-(2-Methoxyethoxy)benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 11 g. of 2-nitro-5-(2-methoxyethoxy) aniline, 220 ml. of methanol, 460 ml. of water, 40 g. sodium carbonate and 60 g. sodium hydrosulfite is refluxed for 15 minutes. The solution is concentrated, diluted with water and extracted with chloroform. Evaporation of the chloroform leaves 1,2-diamino-4-(2-methoxyethoxy) benzene as an oil, sufficiently pure for the next step.

Workup

  1. additionA mixture of 11 g
  2. concentrationThe solution is concentrated
  3. additiondiluted with water
  4. extractionextracted with chloroform
  5. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-1bc0b32cd2d1475db84c7bfe7a8b0a26
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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