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

HRID 981192Notes

Reaction equation

HRID 981192 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

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 14853337Ethyl 3-(2-chloro-6,7-difluoro-3-quinolyl)-3-oxopropionate

Product 1

HCID 53731972Ethyl 2-(2-chloro-6,7-difluoroquinoline-3-carbonyl)-3-dimethylaminoacrylateYield 91.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 6.17 g of ethyl 3-(2-chloro-6,7-difluoro-3-quinolyl)-3-oxopropionate in 7.15 g of N,N-dimethylformamide dimethyl acetal and 60 cm3 of ethyl acetate is heated at a temperature close to 75° C. for 1 hour 15 minutes. The reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at about 50° C. The residue is taken up in 50 cm3 of diisopropyl ether, drained and washed with 3 times 25 cm3 of the same solvent. 6.65 g of ethyl 2-(2-chloro-6,7-difluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate are obtained in the form of an orange solid melting at 140° C.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 75° C. for 1 hour 15 minutes
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at about 50° C
  4. washwashed with 3 times 25 cm3 of the same solvent

Sources & evidence

ORD record
ord-3cbe63ccab774568a669305cd38be4b6
Source dataset
uspto-grants-1991_02
Patent number
US04990515

Reaction notes

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