Methanol → Methyl 2-chloro-4-(methylamino)-5-nitrobenzoate

HRID 1189685Notes

Reaction equation

HRID 1189685 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:14]=[C:13]([NH:15][CH3:16])[C:12]([N+:17]([O-:19])=[O:18])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].[CH3:20]O>>[CH3:20][O:9][C:8](=[O:10])[C:7]1[CH:11]=[C:12]([N+:17]([O-:19])=[O:18])[C:13]([NH:15][CH3:16])=[CH:14][C:6]=1[Cl:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 679575072-Chloro-4-(methylamino)-5-nitrobenzoic acid

Product 1

HCID 67957559Methyl 2-chloro-4-(methylamino)-5-nitrobenzoate

Procedure

Thionylchloride (3.87 g, 32 mmol) is added dropwise at rt to a mixture of 2-chloro-4-methylamino-5-nitro-benzoic acid (5.00 g, 22 mmol) and 45 mL MeOH and it is stirred at reflux overnight. The mixture is cooled to rt and the precipitate is collected by filtration and dried. Yield: 5.01 g. MS m/z: 245 [M+H]+.

Workup

  1. temperatureat reflux overnight
  2. filtrationthe precipitate is collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-17cd38c7ba6c4b629211428c8b58e90a
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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