Trifluoroacetic acid → HCID 59544189, compound

HRID 2425573Notes

Reaction equation

HRID 2425573 reaction equation
[F:1][C:2]([F:24])([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]([O:19]C(C)(C)C)=[O:18])[CH:13]=2)[N:8]=1)[C:3]([F:6])([F:5])[F:4].FC(F)(F)C(O)=O>ClCCl>[F:24][C:2]([F:1])([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]([OH:19])=[O:18])[CH:13]=2)[N:8]=1)[C:3]([F:6])([F:5])[F:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86646795HCID 86646795, compound

Product 1

HCID 59544189HCID 59544189, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-pentafluoroethylquinoline-6-carboxylate (165 mg, 0.475 mmol) in dichloromethane (5 mL), cooled to 0° C., was added trifluoroacetic acid (2 mL, 26 mmol) and the reaction mixture allowed to warm to room temperature and stirred for 16 h. The reaction mixture was concentrated under reduced pressure to give the crude product, 2-pentafluoroethylquinoline-6-carboxylic acid (140 mg, 100%). 1H NMR (400 MHz, CDCl3+2drops CD3OD) δ 7.79 (1H, d), 8.26 (1H, d), 8.39 (1H, dd), 8.47 (1H, d), 8.67 (1H, d). LCMS: Retention time: 1.49 min. MS (ESI) m/z 292 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-488a70094e0647ecb2d01493f886b85b
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

Loading…