Hydrochloric Acid → Methyl 5-amino-2-fluorobenzoate

HRID 2379186Notes

Reaction equation

HRID 2379186 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].Cl.[CH3:13]O>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:13])=[O:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 27359105-Amino-2-fluorobenzoic acid

Product 1

HCID 15621043Methyl 5-amino-2-fluorobenzoate

Procedure

5-Amino-2-fluorobenzoic acid (100 g) was suspended in 1.3 liters of methanol, 100 g of concentrated hydrochloric acid was gradually added thereto and the mixture was heated to reflux for 24 hours. Methanol was evaporated and the residue was poured into ice water, the mixture was neutralized with sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The crystals separated out therefrom were filtered to give 88 g of methyl 5-amino-2-fluorobenzoate.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 24 hours
  3. customMethanol was evaporated
  4. additionthe residue was poured into ice water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. customevaporated
  9. customThe crystals separated out
  10. filtrationtherefrom were filtered

Sources & evidence

ORD record
ord-7738c4b44e5b4710a31771a137cbd3a5
Source dataset
uspto-grants-1994_11
Patent number
US05360822

Reaction notes

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