Hydrochloric Acid → Methyl 2-amino-3-nitrobenzoate

HRID 1012058Notes

Reaction equation

HRID 1012058 reaction equation
C[O-].[Na+].[CH3:4][O:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[NH:16]C(=O)C.Cl>CO>[CH3:4][O:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[NH2:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2782278Methyl 2-acetamido-3-nitrobenzoateHCID 10942334Sodium Methoxide

Product 1

HCID 607264Methyl 2-amino-3-nitrobenzoateYield 64.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (1.50 g, 27.7 mmol) was added to a solution of methyl-2-(acetylamino)-3-nitrobenzoate (1.0 g, 4.2 mmol) in MeOH (30 ml) and the mixture stirred at ambient temperature under nitrogen for 16 h. The reaction was cautiously acidified with concentrated hydrochloric acid then heated at reflux overnight, followed by evaporation and re-evaporation by toluene (2×30 ml). The residue was treated with CH2Cl2 (50 ml), the insoluble material removed through filtration and the filtrate reduced in vacuo. The residue was purified by flash column chromatography [SiO2, EtOAc-hexane (1:4, 1:0)] affording methyl-2-amino-3-nitrobenzoate (535 mg) as a bright yellow solid.

Workup

  1. temperaturethen heated
  2. temperatureat reflux overnight
  3. customfollowed by evaporation and re-evaporation by toluene (2×30 ml)
  4. additionThe residue was treated with CH2Cl2 (50 ml)
  5. customthe insoluble material removed through filtration
  6. customThe residue was purified by flash column chromatography [SiO2, EtOAc-hexane (1:4, 1:0)]

Sources & evidence

ORD record
ord-a9863efc244c44b1a7f16048054bc17a
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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