Hydrochloric Acid → 2-Amino-4-nitro-5-methoxybenzoic Acid

HRID 887903Notes

Reaction equation

HRID 887903 reaction equation
C([NH:4][C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([O:17][CH3:18])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=O)C.Cl>O>[NH2:4][C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([O:17][CH3:18])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 212603512-Acetamido-5-methoxy-4-nitrobenzoic acid2×

Product 1

HCID 212602732-Amino-4-nitro-5-methoxybenzoic AcidYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.5 g of 2-acetylamino-5-methoxy-4-nitrobenzoic acid (crude mixture from stage c) were heated to reflux in 50 ml of water and 20 ml of concentrated hydrochloric acid for 3 hours. The reaction mixture was concentrated in vacuo and purified by column chromatography (silica gel, dichloromethane/isopropanol=9/1). 3.1 g (50%) of the desired product were obtained.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography (silica gel, dichloromethane/isopropanol=9/1)

Sources & evidence

ORD record
ord-2d4c54c9a5874e04ad856f43071f09e9
Source dataset
uspto-grants-2012_08
Patent number
US08247452B2

Reaction notes

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