Triethylamine → 6-Chloro-3-dimethylaminomethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

HRID 653118Notes

Reaction equation

HRID 653118 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:7][CH2:6][C:5]2=[O:16].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21].C(N(CC)CC)C>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:7][C:6](=[CH:19][N:20]([CH3:22])[CH3:21])[C:5]2=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 145014226-Chloro-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 544539906-Chloro-3-dimethylaminomethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinolineYield 82%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 6-chloro-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (2 g), N,N-dimethylformamide dimethyl acetal (7.009 g), and triethylamine (0.87 g) in benzene (50 ml) was refluxed with stirring for 1 hour and then about three-fourths of the solvent was distilled slowly at atmospheric pressure over a period of approximately 1 hour. To the residue was added benzene (100 ml) and the solvent was distilled again. The resulting solid was collected by filtration, washed with diethyl ether, and dried to give 6-chloro-3-dimethylaminomethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (2.02 g).

Workup

  1. distillationabout three-fourths of the solvent was distilled slowly at atmospheric pressure over a period of approximately 1 hour
  2. additionTo the residue was added benzene (100 ml)
  3. distillationthe solvent was distilled again
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-14925182b3fd40b89370b82a539946d3
Source dataset
uspto-grants-1987_06
Patent number
US04675324

Reaction notes

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