Phosphorus oxychloride → HCID 57970207, compound

HRID 1666657Notes

Reaction equation

NN1CCCC1.[CH3:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][C:19]([F:22])([F:21])[F:20])[CH:16]=2)[NH:11][C:10](=O)[CH:9]=1.P(Cl)(Cl)([Cl:26])=O>O>[Cl:26][C:10]1[CH:9]=[C:8]([CH3:7])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][C:19]([F:22])([F:21])[F:20])[CH:16]=2)[N:11]=1

Participants

Conditions

Temperature: 105 °C

Procedure

4-(Trifluoromethoxy)aniline (10 mL) was added dropwise to ethyl acetoacetate (44 mL) at 160° C., and the mixture was stirred at the same temperature for 1 h. The mixture was left stand for cooling to room temperature and crystallized with hexane to obtain 3-oxo-N-(4-(trifluoromethoxy)phenyl)butane amide (6.5 g). (2) To concentrated sulfuric acid (32.5 mL) was added 3-oxo-N-(4-(trifluoromethoxy)phenyl)butane amide (6.5 g), and the mixture was stirred at 95° C. for 3 h. The reaction solution was added dropwise to water with ice cooling, and the precipitated crystals were collected by filtration. The resulting crystals were suspended in water, the suspension was made basic with aqueous ammonia, and the precipitated crystals were collected by filtration to obtain 4-methyl-6-(trifluoromethoxy)quinoline-2(1H)-one (1.87 g). (3) A mixture of 4-methyl-6-(trifluoromethoxy)quinoline-2(1H)-one (1.87 g) and phosphorus oxychloride (19 mL) was stirred at 105° C. for 2.5 h. The reaction solution was added dropwise to water with ice cooling, and the precipitated crystals were collected by filtration to obtain 2-chloro-4-methyl-6-trifluoromethoxyquinoline (1.98 g).

Workup

filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-653de538b86044bc94a2f68b24eb5fe3
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044068B2

Reaction notes

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