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

HRID 35668Notes

Reaction equation

HRID 35668 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](C)[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][NH:20][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 542284186-Chloro-3-methylaminomethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinolineYield 86.1%

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 m) was refluxed with stirring for 1 hour and then about three-fourths of the solvent was distilled slowly at atmospheric pressure over a period ximately 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-methylaminomethylene-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 ximately 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-a0798f33254e49d4856614cee3bd6850
Source dataset
uspto-grants-1988_08
Patent number
US04767780

Reaction notes

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