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

HRID 1050860Notes

Reaction equation

HRID 1050860 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-d207e001abef412ca0f3d7926fdd3990
Source dataset
uspto-grants-2016_07
Patent number
US09387202B2

Reaction notes

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