Water → HCID 20301865, compound

HRID 2164038Notes

Reaction equation

HRID 2164038 reaction equation
[Cl:1][C:2]1[C:8](Cl)=[C:7]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:13][O-:14].[Na+].O>CO>[Cl:1][C:2]1[C:8]([O:14][CH3:13])=[C:7]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

5

Reactant 3

HCID 962WaterHCID 30139982,3-dichloro-4-nitroanilineHCID 10942334Sodium Methoxide

Product 1

HCID 20301865HCID 20301865, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,3-dichloro-4-nitroaniline (25 g) and sodium methoxide (25 g) in methanol (250 ml) is stirred and heated at reflux under a nitrogen atmosphere for 5.5 hours. The reaction mixture is poured into water (1.5 l), the precipitated yellow solid is collected and dried. This material is purified by chromatography on silica gel using 1:1 hexane/ether eluent. The eluents are collected and evaporated to dryness to afford 13 g of title compound, m.p. 118°-123° C.

Workup

  1. temperatureheated
  2. temperatureat reflux under a nitrogen atmosphere for 5.5 hours
  3. customthe precipitated yellow solid is collected
  4. customdried
  5. customThis material is purified by chromatography on silica gel using 1:1 hexane/ether eluent
  6. customThe eluents are collected
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-1806ebde1e544dfab62a7370e1df1492
Source dataset
uspto-grants-1979_01
Patent number
US04137310

Reaction notes

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