Water → 8-(Difluoromethyl)quinoline-5-carboxylic acid

HRID 1795747Notes

Reaction equation

[F:1][CH:2]([F:17])[C:3]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:6]([C:13]([O:15]C)=[O:14])=[CH:5][CH:4]=1.[OH-].[Na+].O>C(O)C>[F:17][CH:2]([F:1])[C:3]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:6]([C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 25 °C

Procedure

0.5 g (2.0 mmol) of methyl 8-difluoromethyl-5-quinolinecarboxylate was dissolved in 5 ml of ethanol, 0.43 g (10.5 mmol) of sodium hydroxide and 1 ml of water were added, and the mixture was stirred at 25° C. for 20 hours. The solvents were subsequently removed, the residue was taken up in water, washed twice with methylene chloride and adjusted to pH 1 using 10 N hydrochloric acid, and the precipitate was filtered off with suction. Drying gave 0.5 g of 8-difluoromethyl-5-quinolinecarboxylic acid (colorless crystals);

Workup

customThe solvents were subsequently removed
washwashed twice with methylene chloride
filtrationthe precipitate was filtered off with suction
customDrying

Sources & evidence

ORD record: ord-daca5a902b094c5cb160bdc9bd25377e
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030063B1

Reaction notes

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