Methanol → HCID 86700080, compound

HRID 1428127Notes

Reaction equation

HRID 1428127 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13](=[O:21])[C:14]([C:18]([OH:20])=[O:19])=[CH:15][NH:16][CH:17]=2)=[CH:8][CH:7]=1.[CH3:22]O>>[F:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[C:13](=[O:21])[C:14]([C:18]([O:20][CH3:22])=[O:19])=[CH:15][NH:16][CH:17]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 602042075-(4-Fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid

Product 1

HCID 86700080HCID 86700080, compound

Conditions

Temperature
70 °C

Procedure

Thionyl chloride (0.8 ml) was added to a suspension of 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid (400 mg) in methanol (9 ml) at 0° C. The reaction mixture was stirred at 70° C. overnight. The reaction mixture was returned to room temperature and concentrated under reduced pressure. The resulting residue was washed with saturated aqueous sodium bicarbonate and water, and then further washed with diethyl ether to give 304 mg of the title compound as a solid.

Workup

  1. customwas returned to room temperature
  2. concentrationconcentrated under reduced pressure
  3. washThe resulting residue was washed with saturated aqueous sodium bicarbonate and water
  4. washfurther washed with diethyl ether

Sources & evidence

ORD record
ord-f2135e78b589452fb023e913bb994a37
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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