Hydrochloric Acid → 1-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 1046016Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16]C)=[O:15])[C:9]2=[O:18])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[C:9]2=[O:18])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of methyl 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (14 g, 58.4 mmol) and 2N aqueous NaOH (90 mL) in methanol (150 mL) was heated at 65° C. overnight. The cooled reaction mixture was treated with 2N HCl solution with stirring until pH=1. The precipitate that formed was collected by filtration, washed with water (10 mL), and dried to give 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (7.0 g, 53% yield). 1H-NMR (400 MHz, MeOH-d4): δ 8.58 (dd, J=7.2, 2.0 Hz, 1H), 8.04 (dd, J=6.8, 2.0 Hz, 1H), 7.53 (m, 2H), 7.31 (m, 2H), 6.83 (t, J=7.2 Hz, 1H).

Workup

customThe cooled reaction mixture
customThe precipitate that formed
filtrationwas collected by filtration
washwashed with water (10 mL)
customdried

Sources & evidence

ORD record: ord-0903eef24e014c04b4d082093d992f8d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569319B2

Reaction notes

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