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Methanol → 2-(2,2,2-Trifluoro-1,1-dimethyl-ethyl)-quinoline-6-carboxylic acid

HRID 1693076
Notes
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Reaction equation

HRID 1693076 reaction equation
CO.[F:3][C:4]([F:23])([F:22])[C:5]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([O:20]C)=[O:19])[CH:14]=2)[N:9]=1)([CH3:7])[CH3:6].[OH-].[Na+]>C1COCC1>[F:23][C:4]([F:3])([F:22])[C:5]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([OH:20])=[O:19])[CH:14]=2)[N:9]=1)([CH3:7])[CH3:6]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57458169Methyl 2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline-6-carboxylate

Product 1

HCID 574581632-(2,2,2-Trifluoro-1,1-dimethyl-ethyl)-quinoline-6-carboxylic acidYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A methanol (6 ml) and THF (6 ml) solution of methyl 2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline-6-carboxylate (777 mg, 2.6 mmol) and 2M sodium hydroxide aqueous solution (2.6 ml, 5.2 mmol) was treated in the procedure described in Step C-2C to furnish the title compound (735 mg, 99% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.75 (6H, s), 7.74 (1H, d, J=8.8 Hz), 8.19 (1H, d, J=8.8 Hz), 8.29 (1H, d, J=8.8 Hz), 8.35-8.40 (1H, m), 8.69-8.70 (1H, m). MS (ESI): m/z 284 (M+H)+.

Sources & evidence

ORD record
ord-592027b607144ebe9d32c185f59bc213
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08158650B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes