4-Methylbenzoyl Chloride → HCID 14049609, compound

HRID 466153Notes

Reaction equation

HRID 466153 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl:11][C:12]1[C:13]([OH:19])=[CH:14][C:15](=[O:18])[NH:16][CH:17]=1>N1C=CC=CC=1>[Cl:11][C:12]1[C:13]([O:19][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:14][C:15]([O:18][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=2)=[N:16][CH:17]=1

Participants

4

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 54679224Gimeracil

Product 1

HCID 14049609HCID 14049609, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 2.66 g quantity of 4-methylbenzoyl chloride was added dropwise to 50 ml of a solution of 1.00 g of 5-chloro-4-hydroxy-2-pyridone in pyridine. The mixture was subjected to reaction at room temperature overnight. The pyridine was distilled off and the residue was stirred in ether for 6 hours. The solids thus precipitated were dried, giving 1.71 g of the title compound. The ether was concentrated and the residue was applied to silica gel column chromatography using as an eluent petroleum ether-chloroform (1:2), affording 0.85 g of the same compound (total amount 2.56 g, total yield 97%).

Workup

  1. customThe mixture was subjected to reaction at room temperature overnight
  2. distillationThe pyridine was distilled off
  3. customThe solids thus precipitated
  4. customwere dried

Sources & evidence

ORD record
ord-8aa9969224bf4bc293d9ce25c13809d7
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

Loading…