2-Acetamido-5-methoxy-4-nitrobenzoic acid → 2-Amino-4-nitro-5-methoxybenzoic Acid

HRID 634740Notes

Reaction equation

HRID 634740 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>O.Cl>[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 1

HCID 212603512-Acetamido-5-methoxy-4-nitrobenzoic acid

Product 1

HCID 212602732-Amino-4-nitro-5-methoxybenzoic AcidYield 92%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-acetamido-5-methoxy-4-nitrobenzoic acid (21.6 g, 85 mmol) in water (76 ml) and concentrated hydrochloric acid (30.5 ml) was heated at reflux for 3 hours. The reaction mixture was cooled to 0° C., the resulting solid was collected by filtration, washed with water and dried under vacuum to give 2-amino-5-methoxy-4-nitrobenzoic acid (I 6.6 g, 92%).

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationthe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-81d073c9ba1f4d358902b3c0b4520d2f
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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