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

HRID 981182Notes

Reaction equation

HRID 981182 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

Procedure

A suspension of 16.5 g of ethyl 3-(2,7-dichloro-6-fluoro-3-quinolyl)-3-oxopropionate in 160 cm3 of ethyl acetate and 19 cm3 of N,N-dimethylformamide dimethyl acetal is heated at a temperature close to 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 in 50 cm3 of diisopropyl ether, drained and washed with twice 10 cm3 of diisopropyl ether. 16.57 g of ethyl 2-(2,7-dichloro-6-fluoro-quinoline-3-carbonyl)-3-dimethylaminoacrylate are obtained in the form of an orange solid melting at 122° C. This product is used for the subsequent steps without further purification.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 75° C.
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at 50° C
  4. extractionThe dry extract
  5. washwashed with twice 10 cm3 of diisopropyl ether

Sources & evidence

ORD record
ord-0e1fe1d67f004a3bac4a7acfbd404297
Source dataset
uspto-grants-1991_02
Patent number
US04990515

Reaction notes

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