Trifluoroacetic acid → 2-(Trifluoromethyl)quinoline-6-carboxylic acid

HRID 2425572Notes

Reaction equation

HRID 2425572 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([O:15]C(C)(C)C)=[O:14])[CH:9]=2)[N:4]=1.FC(F)(F)C(O)=O>ClCCl>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([OH:15])=[O:14])[CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58118637HCID 58118637, compound

Product 1

HCID 450732972-(Trifluoromethyl)quinoline-6-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-trifluoromethylquinoline-6-carboxylate (2 g, 7 mmol) in dichloromethane (50 mL), cooled to 0° C., was added trifluoroacetic acid (5.18 mL, 67.2 mmol) and the reaction mixture allowed to warm to room temperature and stirred for 36 h. The reaction mixture was concentrated under reduced pressure and the crude product obtained triturated with heptane (4×10 mL) to give 2-trifluoromethylquinoline-6-carboxylic acid (1.58 g, 98%). 1H NMR (400 MHz, CD3OD) δ 7.93 (1H, d), 8.24 (1H, d), 8.42 (1H, dd), 8.73 (1H, d), 8.78 (1H, d). LCMS: Retention time: 1.38 min. MS (ESI) m/z 242 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude product obtained
  3. customtriturated with heptane (4×10 mL)

Sources & evidence

ORD record
ord-17166673b664423cbfce76ef5c6fe369
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

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