1-Cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-3-quinolinecarbonitrile → 1-Cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-3-quinolinecarbaldehyde

HRID 1828559Notes

Reaction equation

[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([F:14])[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]#N)=[CH:5]2)[CH2:3][CH2:2]1.O.[PH2](=O)[O-:21].[Na+]>C(O)(=O)C.O.N1C=CC=CC=1.[Ni]>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([F:14])[CH:12]=3)[C:7](=[O:16])[C:6]([CH:17]=[O:21])=[CH:5]2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

The 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-3-quinolinecarbonitrile (150 mg, 0.609 mmol) obtained in (B) was dissolved in a mixed solution of acetic acid, water and pyridine (1:1:2, 4 ml), added with Raney Nickel (catalytic amount) and sodium phosphinate monohydrate (258 mg, 2.44 mmol), and then the mixture was stirred overnight at 60° C. The reaction mixture was left stand for cooling and the catalyst was removed by filtration through a Celite layer and washed with hot ethanol. The reaction mixture was concentrated, then diluted with chloroform, and washed with aqueous copper sulfate. The organic layer was dried over anhydrous magnesium sulfate to obtain the title compound (97.0 mg, 64%) as pale yellow solid.

Workup

waitThe reaction mixture was left stand
temperaturefor cooling
customthe catalyst was removed by filtration through a Celite layer
washwashed with hot ethanol
concentrationThe reaction mixture was concentrated
additiondiluted with chloroform
washwashed with aqueous copper sulfate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record: ord-f95dcef9ef304c029a13f1837736e815
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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