Benzylamine → Benzoic acid, 6-amino-2,3,4-trifluoro-, methyl ester (9CI)

HRID 5570Notes

Reaction equation

HRID 5570 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[CH:9]=[C:8](F)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([NH2:22])C1C=CC=CC=1>C1C=CC=CC=1>[NH2:22][C:8]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[C:11]([F:12])=[C:10]([F:13])[CH:9]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 20078034Methyl 2,3,4,6-tetrafluorobenzoate

Product 1

HCID 20077977Benzoic acid, 6-amino-2,3,4-trifluoro-, methyl ester (9CI)

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

60 g of methyl 2,3,4,6-tetrafluorobenzoate and 70 g of benzylamine were reacted under reflux for 1 hour in 400 ml of benzene. After the reaction mixture was allowed to cool down, it was washed successively with water, 1% hydrochloric acid and 1% aq. sodium carbonate, each in the amount of 600 ml. The reaction mixture was treated with anhydrous magnesium sulfate and then concentrated. Crystals thus precipitated were collected by filtration and thereafter washed with methanol. 30 g of the crystals and about 2 ml of palladium/carbon were added to a liquid mixture which consisted of 100 ml of acetic acid and 200 ml of methanol. The resultant mixture was hydrogenated for 1.5 hours. The catalyst was filtered off and the filtrate was concentrated, whereby methyl 6-amino-2,3,4-trifluorobenzoate was obtained as a crystalline residue.

Workup

  1. temperatureto cool down
  2. washit was washed successively with water, 1% hydrochloric acid and 1% aq. sodium carbonate
  3. additionThe reaction mixture was treated with anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customCrystals thus precipitated
  6. filtrationwere collected by filtration
  7. washwashed with methanol
  8. addition30 g of the crystals and about 2 ml of palladium/carbon were added to a liquid mixture which
  9. filtrationThe catalyst was filtered off
  10. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-39ba3d3ec92e459f80ce36b757f83647
Source dataset
uspto-grants-1993_09
Patent number
US05245037

Reaction notes

Loading…