Oxalyl chloride → 2-[(8-Difluoromethylquinolin-5-yl)carbonyl]-1-chloro-4,4,6,6-tetramethyl-cyclohex-1-ene-3,5-dione

HRID 1795749Notes

Reaction equation

[F:1][CH:2]([F:28])[C:3]1[CH:4]=[CH:5][C:6]([C:13]([CH:15]2[C:20](=[O:21])[C:19]([CH3:23])([CH3:22])[C:18](=[O:24])[C:17]([CH3:26])([CH3:25])[C:16]2=O)=[O:14])=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2.C(Cl)(=O)C([Cl:32])=O>ClCCl.CN(C)C=O>[F:1][CH:2]([F:28])[C:3]1[CH:4]=[CH:5][C:6]([C:13]([C:15]2[C:20](=[O:21])[C:19]([CH3:23])([CH3:22])[C:18](=[O:24])[C:17]([CH3:26])([CH3:25])[C:16]=2[Cl:32])=[O:14])=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2

Participants

Conditions

Temperature: 25 °C

Procedure

0.25 g (0.65 mmol) of 2-(8-difluoromethylquinolin-5-yl)carbonyl-4,4,6,6-tetramethyl-cyclohexane-1,3,5-trione was dissolved in 15 ml of dichloromethane and 0.25 g (1.95 mmol) of oxalyl chloride and 7 drops of dimethylformamide were added. The mixture was stirred at 25° C. for 17 hours, after which the solvent was removed. This gave 0.2 g of colorless crystals.

Workup

customafter which the solvent was removed

Sources & evidence

ORD record: ord-fdb4cb6fdf35452f99aa385c3135810b
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030063B1

Reaction notes

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