Dimethylformamide dimethyl acetal → Ethyl 2-(2-chloro-6,7,8-trifluoro-3-quinolinecarbonyl)(dimethylamino)acrylate

HRID 344884Notes

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](=[C:5]([F:22])[C:6]([F:21])=[C:7]([F:20])[CH:8]=2)[N:3]=1.CO[CH:25](OC)[N:26]([CH3:28])[CH3:27]>C(OCC)(=O)C>[Cl:1][C:2]1[C:11]([C:12]([C:13](=[CH:25][N:26]([CH3:28])[CH3:27])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:19])=[CH:10][C:9]2[C:4](=[C:5]([F:22])[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-6,7,8-trifluoro-3-quinolyl)-3-oxopropionate (26.7 g) in ethyl acetate (270 cc) and N,N-dimethylformamide dimethyl acetal (32 cc) is heated to a temperature in the region of 75° C. with stirring for 2 hours. The reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C. The dry extract is taken up with isopropyl ether (175 cc), drained and washed with the same solvent (2×85 cc). Ethyl 2-(2-chloro-6,7,8-trifluoro-3-quinolinecarbonyl)-3-(dimethylamino)acrylate (19.32 g) is obtained in the form of an orange-colored solid, m.p. 118° C., which is used without further purification for the subsequent steps.

Workup

concentrationThe reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C
extractionThe dry extract
washwashed with the same solvent (2×85 cc)

Sources & evidence

ORD record: ord-29d3576f5bb84c8fa67c1ddf84dfc75f
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053509

Reaction notes

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