Hydrochloric Acid → 2-Amino-3-nitrobenzoic acid

HRID 1012061Notes

Reaction equation

HRID 1012061 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[NH:13]C(=O)C.Cl>CCO>[NH2:13][C:5]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:17])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2782278Methyl 2-acetamido-3-nitrobenzoate

Product 1

HCID 2196332-Amino-3-nitrobenzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl-2-(acetylamino)-3-nitrobenzoate (2.6 g) in EtOH (50 ml) was treated with concentrated hydrochloric acid (10 ml) then heated at reflux for 16 h. The reaction mixture was cooled, reduced in vacuo and azeotroped with toluene (2×50 ml) to give 2-amino-3-nitrobenzoic acid (1.83 g) as a bright yellow solid.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 16 h
  3. temperatureThe reaction mixture was cooled
  4. customazeotroped with toluene (2×50 ml)

Sources & evidence

ORD record
ord-c7031e618c51458da31e5f11aec1d403
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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