Cyanuric chloride → 7-FLUORO-6-METHOXY-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBONITRILE

HRID 1837328Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12]([NH2:14])=O)=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:16][CH3:17].N1C(Cl)=NC(Cl)=NC=1Cl.C(=O)(O)[O-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12]#[N:14])=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:16][CH3:17]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 7-fluoro-6-methoxy-4-oxo-1,4,-dihydro-3-quinolinecarboxamide (700 mg, 3.0 mmol) and cyanuric chloride (341 mg, 1.65 mmol) in 15 mL of N,N,-dimethylformamide is heated at 65° C. for 6 hours then cooled to room temperature and an additional 206 mg of cyanuric chloride is added. The mixture is heated at 65° C. for 4 hours then stirred overnight at room temperature. The reaction mixture is poured into ice water and neutralized with saturated sodium bicarbonate. The solids are collected by filtration washing with water and hexane to provide 610 mg of crude product. Purification by flash column chromatography eluting with a gradient of 3% methanol in dichloromethane to 10% methanol in dichloromethane, provides 272 mg of 7-fluoro-6-methoxy-4-oxo-1,4-dihydro-3-quinolinecarbonitrile, mp 147-149° C.

Workup

temperaturethen cooled to room temperature
temperatureThe mixture is heated at 65° C. for 4 hours
filtrationThe solids are collected by filtration
washwashing with water and hexane
customto provide 610 mg of crude product
customPurification by flash column chromatography
washeluting with a gradient of 3% methanol in dichloromethane to 10% methanol in dichloromethane

Sources & evidence

ORD record: ord-3c1bad142b3c4e9794358d566fb1eef7
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780996B2

Reaction notes

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