Methanol → Benzoic acid, 3-amino-, methyl ester

HRID 2205166Notes

Reaction equation

HRID 2205166 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10].[CH3:15]O>>[NH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([O:11][CH3:15])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 74193-Aminobenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 78274Benzoic acid, 3-amino-, methyl esterYield 93%

Procedure

Thionyl chloride (43 g, 361.34 mmol, 5.00 equiv) was added dropwise with stirring at 0° C. to a solution of 3-aminobenzoic acid (10 g, 72.92 mmol, 1.00 equiv) in methanol (100 mL) and allowed to react, with stifling, overnight under reflux. The resulting mixture was concentrated under vacuum and quenched by the addition of 50 mL of water/ice. The resulting solids were collected via vacuum filtration and dried in an oven under reduced pressure, affording 10.3 g (93%) of methyl 3-aminobenzoate as a white solid.

Workup

  1. customto react, with stifling, overnight
  2. temperatureunder reflux
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customquenched by the addition of 50 mL of water/ice
  5. filtrationThe resulting solids were collected via vacuum filtration
  6. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-efe8f3781de24aa4b7f32b2eed935d45
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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