Dimethylformamide dimethyl acetal → Ethyl 2-(2,7-dichloro-6-fluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate

HRID 344847Notes

Reaction equation

HRID 344847 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]([Cl: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]([Cl:21])=[C:7]([F:20])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 14726625Ethyl 3-(2,7-dichloro-6-fluoro-3-quinolyl)-3-oxopropionate

Product 1

HCID 54015905Ethyl 2-(2,7-dichloro-6-fluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of ethyl 3-(2,7-dichloro-6-fluoro-3-quinolinyl)-3-oxopropionate (16.5 g) in ethyl acetate (160 cc) and N,N-dimethylformamide dimethyl acetal (19 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 50° C. The dry extract is taken up with isopropyl ether (50 cc), drained and washed with isopropyl ether (2×10 cc). Ethyl 2-(2,7-dichloro-6-fluoro-3-quinolinecarbonyl)-3-(dimethylamino)acrylate (16.57 g) is obtained in the form of an orange-colored solid, m.p. 122° C. This product is used without further purification for the subsequent steps.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at 50° C
  2. extractionThe dry extract
  3. washwashed with isopropyl ether (2×10 cc)

Sources & evidence

ORD record
ord-1c51f1c2cbfd4a1f92da8e8a5a17bb22
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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