Benzylamine → 2-Benzylamino-3,4,6-trifluorobenzoic acid

HRID 373518Notes

Reaction equation

HRID 373518 reaction equation
F[C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[C:7]([F:13])[C:3]=1[C:4]([OH:6])=[O:5].[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCOCC1>[CH2:14]([NH:21][C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[C:7]([F:13])[C:3]=1[C:4]([OH:6])=[O:5])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 27765912,3,4,6-tetrafluorobenzoic Acid

Product 1

HCID 149964422-Benzylamino-3,4,6-trifluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 19.4 g of 2,3,4,6-tetrafluorobenzoic acid, 200 ml of dioxane and 35.3 ml of benzylamine was heated under reflux for 3 hours. The reaction mixture was concentrated to dryness under reduced pressure. Water was added to the residue, and hydrochloric acid was added to adjust the pH of the solution to 3. The solution was then extracted with ethyl acetate. The extract was dried, treated with activated carbon and concentrated. Ether and n-hexane were added to the residue, and the crystals were collected by filtration to give 20.2 g of 2-benzylamino-3,4,6-trifluorobenzoic acid. m.p. 140-141° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. additionWater was added to the residue, and hydrochloric acid
  5. additionwas added
  6. extractionThe solution was then extracted with ethyl acetate
  7. customThe extract was dried
  8. additiontreated with activated carbon
  9. concentrationconcentrated
  10. additionEther and n-hexane were added to the residue
  11. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-48494852f08d407f89ea6f7804b0ba24
Source dataset
uspto-grants-1992_11
Patent number
US05164392

Reaction notes

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