Trifluoroacetic acid → HCID 68755585, compound

HRID 2097957Notes

Reaction equation

HRID 2097957 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[CH:5][C:6]([CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:21][C:2]([F:1])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([CH2:13][C:14]([OH:16])=[O:15])=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 687591091,1-Dimethylethyl 8-(trifluoromethyl)-5-quinolineacetate

Product 1

HCID 68755585HCID 68755585, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(8-(trifluoromethyl)quinolin-5-yl)acetate (400 mg, 1.28 mmol) in DCM (5 mL) was added TFA (10 mL) dropwise. The reaction was stirred at room temperature overnight. After the reaction was complete, the solvent was removed and the residue was purified (silica gel chromatography) to give the final product 2-(8-(trifluoromethyl)quinolin-5-yl)acetic acid (180 mg, 54%). LC-MS (0.05% TFA): [M+1]+ 256.1. 1H-NMR (DMSO-d6, 400 MHz): δ 12.70 (s, 1H), 9.07 (m, 1H), 8.56 (m, 1H), 8.15 (d, 1H), 7.74 (m, 1H), 7.68 (m, 1H), 4.23 (s, 2H). 13C-NMR (DMSO-d6, 100 MHz): δ 171.9, 151.0, 144.0, 138.3, 133.5, 127.87, 127.83, 127.78, 125.3, 123.1, 122.2, 37.7.

Workup

  1. customthe solvent was removed
  2. customthe residue was purified (silica gel chromatography)

Sources & evidence

ORD record
ord-097b91c2f07e446687ca58639290c240
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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