methyl 3-(2-chloro-6-fluorophenyl)-2-hydrazinylidene-3-oxopropanoate → Methyl 5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate

HRID 598154Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[C:9](=[O:17])[C:10](=[N:15][NH2:16])[C:11]([O:13][CH3:14])=[O:12]>COCCOCCOCCOC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[C:9](=[O:17])[C:10]([C:11]([O:13][CH3:14])=[O:12])=[N:15][NH:16]2

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 4.2 g (16 mmol) of methyl 3-(2-chloro-6-fluorophenyl)-2-hydrazono-3-oxopropionate in 12 mL of triglyme was heated to 140° C. for 48 h. The slurry was then cooled to room temperature and the precipitate was collected by filtration. The precipitate was washed with diisopropyl ether and dried in vacuo to give 2.55 g (66%) of the title compound as a tan powder.

Workup

temperatureThe slurry was then cooled to room temperature
filtrationthe precipitate was collected by filtration
washThe precipitate was washed with diisopropyl ether
customdried in vacuo

Sources & evidence

ORD record: ord-a772b97b19494f9aba28cd908cd5b0b6
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

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