Methanol → Methyl 3-amino-5-nitrobenzoate

HRID 1160446Notes

Reaction equation

HRID 1160446 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:18]O>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([O:7][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2393423-Amino-5-nitrobenzoic acid

Product 1

HCID 2756518Methyl 3-amino-5-nitrobenzoateYield 99%

Conditions

Temperature
70 °C

Procedure

To a solution of 3-amino-5-nitrobenzoic acid 10.3 g (56.6 mmol) in methanol (100 mL) was added thionyl chloride 6.5 mL (89 mmol) dropwise under ice-cooing, and the mixture was stirred at 70° C. for 4 hours. The solvent was evaporated and thereto was added water and the mixture was extracted three times with ethyl acetate (100 mL). The organic layer was washed with an aqueous saturated sodium bicarbonate solution and dried on magnesium sulfate, filtered and concentrated to give 11.0 g (56.1 mmol) of methyl 3-amino-5-nitrobenzoate as a brown solid (yield: 99%).

Workup

  1. customThe solvent was evaporated
  2. additionwas added water
  3. extractionthe mixture was extracted three times with ethyl acetate (100 mL)
  4. washThe organic layer was washed with an aqueous saturated sodium bicarbonate solution
  5. customdried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bfc9aa1f3b5b4827964681466480d2a7
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

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