Methanol → Methyl 3-amino-2-fluorobenzoate

HRID 1187301Notes

Reaction equation

HRID 1187301 reaction equation
[NH2:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([NH2:1])[C:3]=1[F:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric Acid2×HCID 230943433-Amino-2-fluorobenzoic acid

Product 1

HCID 46311080Methyl 3-amino-2-fluorobenzoate

Procedure

In a round bottom flask, 3-amino-2-fluoro-benzoic acid (71, 2.51 g, 16.2 mmol) is dissolved in 100 mL of methanol and 1 mL of concentrated sulfuric acid is added. The reaction is heated to reflux for 24 hours and an additional 1 mL of concentrated sulfuric acid is added. The reaction is heated to reflux another 20 hours, then extracted with ethyl acetate and saturated aqueous sodium chloride. The organic layer is isolated and washed with water, sodium bicarbonate, and brine, then dried with magnesium sulfate, and filtered. The filtrate is concentrated under vacuum to provide the desired compound (72, 2.688 g).

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe reaction is heated
  4. temperatureto reflux another 20 hours
  5. extractionextracted with ethyl acetate and saturated aqueous sodium chloride
  6. customThe organic layer is isolated
  7. washwashed with water, sodium bicarbonate, and brine
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-3701941672854ff19d0a6b861aa08e80
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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