Methanol → Methyl 2-amino-4-fluorobenzoate

HRID 2359404Notes

Reaction equation

HRID 2359404 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>>[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 14075433Methyl 2-amino-4-fluorobenzoate

Procedure

To a solution of 2-amino-4-fluorobenzoic acid (2.0 g, 12.9 mmol) in methanol (50 mL) was added thionyl chloride (1.8 mL, 25.8 mmol). The mixture was refluxed overnight and concentrated to dryness. The residue was extracted with CH2Cl2 (30 mL), washed by aq. NaHCO3 (20 mL), water, and brine, dried and concentrated to give methyl 2-amino-4-fluorobenzoate as yellow solid (1.4 g).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationconcentrated to dryness
  3. extractionThe residue was extracted with CH2Cl2 (30 mL)
  4. washwashed by aq. NaHCO3 (20 mL), water, and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1b5c5732b56e409686014dab5bfe2c99
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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