Triethylamine → HCID 86741629, compound

HRID 653120Notes

Reaction equation

HRID 653120 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:14][CH2:13]1)[C:7](=[C:15]=[O:16])[CH2:6][C:5]2=[O:17].CO[CH:20](OC)[N:21]([CH3:23])[CH3:22].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]([CH:12]1[CH2:13][CH2:14]1)[C:7](=[C:15]=[O:16])[C:6](=[CH:20][N:21]([CH3:23])[CH3:22])[C:5]2=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 867416286-Chloro-1-cycloprop yl-carbonyl-4-oxo-1,2,3,4-tetrahydroquinoline

Product 1

HCID 86741629HCID 86741629, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 6-chloro-1-cyclopropyl-carbonyl-4-oxo-1,2,3,4-tetrahydroquinoline (1.996 g), N,N-dimethylformamide dimethyl acetal (3.808 g), and triethylamine (1.212 g) in benzene (16 ml) was refluxed with stirring for 30 minutes and then about three-fourths of the solvent was distilled slowly at atmospheric pressure over a period of approximately 30 minutes. To the residue was added benzene (16 ml) and the solvent was distilled again. The residue was dissolved in ethyl acetate, treated with activated charcoal, and evaporated in vacuo. The residual solid was washed with diethyl ether to give 6-chloro-1-cyclopropyl-carbonyl-3-dimethylaminomethylene-4-oxo-1,2,3,4-tetrahydroquinoline (2.43 g).

Workup

  1. distillationabout three-fourths of the solvent was distilled slowly at atmospheric pressure over a period of approximately 30 minutes
  2. additionTo the residue was added benzene (16 ml)
  3. distillationthe solvent was distilled again
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. additiontreated with activated charcoal
  6. customevaporated in vacuo
  7. washThe residual solid was washed with diethyl ether

Sources & evidence

ORD record
ord-66dc1ba6056d41d4bf207fab094ad123
Source dataset
uspto-grants-1987_06
Patent number
US04675324

Reaction notes

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