Methanol → Methyl 4-nitroanthranilate

HRID 2300970Notes

Reaction equation

HRID 2300970 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:19]O>>[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 120764-Nitroanthranilic acid

Product 1

HCID 596476Methyl 4-nitroanthranilateYield 89%

Procedure

A mixture of 118.8 g of 2-amino-4-nitro-benzoic acid, 1000 ml of methanol and 120 ml of concentrated sulfuric acid is heated at the boiling point for 16 hours. The mixture is concentrated under reduced pressure, the residue is taken up in ethyl acetate and the mixture is washed with saturated NaHCO3 solution. After drying over Na2SO4, the organic phase is concentrated. 114.2 g (89%) of methyl 2-amino-4-nitro-benzoate are thus obtained with a melting point (m.p.) of 156-158° C.

Workup

  1. temperatureis heated at the boiling point for 16 hours
  2. concentrationThe mixture is concentrated under reduced pressure
  3. washthe mixture is washed with saturated NaHCO3 solution
  4. dry with materialAfter drying over Na2SO4
  5. concentrationthe organic phase is concentrated

Sources & evidence

ORD record
ord-99b503fe64e54dbc8367b21a7c93283f
Source dataset
uspto-grants-2002_12
Patent number
US06498253B1

Reaction notes

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