Thionyl Chloride → 1-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chloride

HRID 1472599Notes

Reaction equation

HRID 1472599 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)=[O:15])[C:9]2=[O:17])=[CH:4][CH:3]=1.O=S(Cl)[Cl:20]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([Cl:20])=[O:15])[C:9]2=[O:17])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 210815271-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 596809561-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chlorideYield 100%

Procedure

A solution of 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (prepared according to: J. Med. Chem. (2008), 51, 5330-5341) (0.257 g, 1.1 mmol) in SOCl2 (2.409 mL, 33.0 mmol) was heated to 60° C. for 35 min, cooled to RT and concentrated to dryness. The residue was co-evaporated with toluene (2×) to afford 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chloride (100% yield assumed) as a yellow solid.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6e386f5b262b4adea6a44069e8e41c78
Source dataset
uspto-grants-2015_04
Patent number
US09012635B2

Reaction notes

Loading…