Dimethylformamide dimethyl acetal → Ethyl 2-(2-chloro-6,7-difluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate

HRID 344872Notes

Reaction equation

[Cl:1][C:2]1[C:11]([C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:21])=[C:7]([F:20])[CH:8]=2)[N:3]=1.CO[CH:24](OC)[N:25]([CH3:27])[CH3:26]>C(OCC)(=O)C>[Cl:1][C:2]1[C:11]([C:12]([C:13](=[CH:24][N:25]([CH3:27])[CH3:26])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:19])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:21])=[C:7]([F:20])[CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A suspension of ethyl 3-(2-chloro-6,7-difluoro-3-quinolyl)-3-oxopropionate (6.17 g) in N,N-dimethylformamide dimethyl acetal (7.15 g) and ethyl acetate (60 cc) is heated to a temperature in the region of 75° C. for 1 hour 15 minutes. The reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C. The residue is taken up with isopropyl ether (50 cc), drained and washed with the same solvent (3×25 cc). Ethyl 2-(2-chloro-6,7-difluoro-3-quinolinecarbonyl)-3-(dimethyl amino)acrylate (6.65 g) is obtained in the form of an orange-colored solid, m.p. 140° C.

Workup

concentrationThe reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C
washwashed with the same solvent (3×25 cc)

Sources & evidence

ORD record: ord-c527173924fc4ccfa267b1a9151b595f
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053509

Reaction notes

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