Triethylamine → HCID 10020225, compound

HRID 1588734Notes

Reaction equation

HRID 1588734 reaction equation
[NH2:1][CH:2]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:3]1(C)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=O.[CH2:19](N(CC)CC)C.CC(C(Cl)=O)[C:28](Cl)=[O:29].[C:34]([O:37][CH2:38]C)(=[O:36])[CH3:35]>>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]1[C:3]2[C:2](=[CH:16][C:15]([CH3:19])=[C:14]([CH3:17])[CH:13]=2)[NH:1][C:28](=[O:29])[C:35]=1[C:34]([O:37][CH3:38])=[O:36]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10931669MethylmalonylchlorideHCID 19754480HCID 19754480, compound

Product 1

HCID 10020225HCID 10020225, compoundYield 83.7%

Procedure

To a mixture of 2-amino-2'-chloro-1,5-dimethylbenzophenone (4.0 g), triethylamine (4.3 ml) and ethyl acetate (80 ml) was dropwise added methyl malonyl chloride (3.77 g) under ice-cooling and stirring. The stirring was continued for an hour under ice-cooling. The reaction mixture was washed with water, dried (MgSO4) and distilled to remove the solvent. The oily residue was dissolved in toluene (60 ml), followed by addition of piperidine (0.4 ml). The solution was heated for an hour with removal of water using Dean-Stark's apparatus. Then, the solution was washed with water, dried (MgSO4) and concentrated to obtain crystals of methyl 4-(2-chlorophenyl)-1,2-dihydro-6,7-dimethyl-2-oxo-3-quinolinecarboxylate (4.40 g, 83.7%). Recrystallization from ethanol - chloroform gave colorless prisms. mp 288°-289° C.

Workup

  1. temperaturecooling
  2. waitThe stirring was continued for an hour under ice-
  3. temperaturecooling
  4. washThe reaction mixture was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationdistilled
  7. customto remove the solvent
  8. dissolutionThe oily residue was dissolved in toluene (60 ml)
  9. additionfollowed by addition of piperidine (0.4 ml)
  10. temperatureThe solution was heated for an hour with removal of water using Dean-Stark's apparatus
  11. washThen, the solution was washed with water
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-4b242fd199eb4a58ba5671b91ba3810b
Source dataset
uspto-grants-1993_06
Patent number
US05223513

Reaction notes

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