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

HRID 1411143Notes

Reaction equation

HRID 1411143 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:6](=[O:17])[C:5]=1[C:18]([OH:20])=O)[CH3:2].O=S(Cl)[Cl:23]>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:6](=[O:17])[C:5]=1[C:18]([Cl:23])=[O:20])[CH3:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 585350974-Ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 866675054-Ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

A solution of Example B1 (35 g, 126 mmol) in toluene (400 mL) was treated with SOCl2 (120 g, 1.01 mol) and one drop of DMF, and was heated to reflux for 2 h. The mixture was concentrated in vacuo to afford 4-ethoxy-1-(4-fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl chloride (33.5 g, 100% yield). The residue was carried into the next reaction without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-5d271e5b63834925924ab1bd9442aa74
Source dataset
uspto-grants-2014_12
Patent number
US08921565B2

Reaction notes

Loading…