Sulfuric Acid → Methyl 2-amino-4-chloro-5-nitrobenzoate

HRID 1858171Notes

Reaction equation

HRID 1858171 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Cl:13])=[CH:6][C:5]=1[NH:14]C(=O)C.S(=O)(=O)(O)O>>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Cl:13])=[CH:6][C:5]=1[NH2:14]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 544712152-Acetylamino-4-chloro-5-nitrobenzoic acid methyl ester

Product 1

HCID 15895692Methyl 2-amino-4-chloro-5-nitrobenzoateYield 95%

Procedure

To a solution of 2-acetylamino-4-chloro-5-nitrobenzoic acid methyl ester (1.02 g in 15 mL methanol) was added 1 mL of conc. sulfuric acid and the mixture heated to reflux on an oil bath. After 1 hour, the mixture was concentrated in vacuo and the resulting solid dissolved in 200 mL ethyl acetate. This was then washed with 10% sodium bicarbonate (2×100 mL) and brine (100 mL) and the organics dried over magnesium sulfate. The concentrate was recrystallized from methanol to give the title compound (0.82 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionthe resulting solid dissolved in 200 mL ethyl acetate
  5. washThis was then washed with 10% sodium bicarbonate (2×100 mL) and brine (100 mL)
  6. dry with materialthe organics dried over magnesium sulfate
  7. customThe concentrate was recrystallized from methanol

Sources & evidence

ORD record
ord-9bf305f439164456852fecce9970376e
Source dataset
uspto-grants-2000_11
Patent number
US06150522

Reaction notes

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