HCID 53913940, compound → HCID 54427475, compound

HRID 1109429Notes

Reaction equation

HRID 1109429 reaction equation
[F:1][C:2]([F:25])([F:24])[CH:3]([O:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>C(O)C.[Pd]>[F:1][C:2]([F:24])([F:25])[CH:3]([O:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 1

HCID 53913940HCID 53913940, compound

Product 1

HCID 54427475HCID 54427475, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The reaction liquid was poured into water, and extracted with methylene chloride. The methylene chloride layer was washed with a diluted hydrochloric acid and water in this order. The organic layer thus recovered was distilled under a reduced pressure to remove the solvent, and subjected to purification by a silica gel chromatography (n-hexane:ethyl acetate=10:2) to obtain 2.1 g of p-nitrobenzoic acid 1,1,1-trifluoro-2-decyl ester. The ester was dissolved in 30 ml of ethanol, to which 0.21 g of 5 % Pd-C catalyst was added, and the solution was stirred overnight under hydrogen atmosphere, then the Pd-C catalyst was separated by filtration, and the ethanol was distilled off under a reduced pressure to obtain 2.0 g of p-amino-benzoic acid 1,1,1-trifluoro-2-decyl ester which was the desired compound of the reaction [1].

Workup

  1. additionwas added
  2. customthe Pd-C catalyst was separated by filtration
  3. distillationthe ethanol was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-199757cb80f247d496050b288ce926e1
Source dataset
uspto-grants-1994_06
Patent number
US05320776

Reaction notes

Loading…