Triethylamine → HCID 10448748, compound

HRID 1588739Notes

Reaction equation

HRID 1588739 reaction equation
[NH2:1][C:2]1[CH:16]=[C:15]([CH3:17])[C:14]([CH3:18])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=O.C(N(CC)CC)C.CC(C(Cl)=O)[C:28](Cl)=[O:29].[C:34]([O:37][CH2:38]C)(=[O:36])[CH3:35]>>[CH3:18][C:14]1[CH:13]=[C:3]2[C:2](=[CH:16][C:15]=1[CH3:17])[NH:1][C:28](=[O:29])[C:35]([C:34]([O:37][CH3:38])=[O:36])=[C:4]2[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10931669MethylmalonylchlorideHCID 19754477HCID 19754477, compound

Product 1

HCID 10448748HCID 10448748, compound

Procedure

To a mixture of 2-amino-4,5,2'-trimethylbenzophenone (4.8 g), triethylamine (5.6 ml) and ethyl acetate (80 ml) was dropwise added methyl malonyl chloride (4.88 g) under ice-cooling and stirring. The mixture was stirred for an hour under ice-cooling, washed with water, dried (MgSO4) and concentrated to remove the solvent. The oily product was dissolved in toluene (60 ml), and DBU (0.3 g) was added to the solution. The solution was refluxed for 30 minutes with removal of water using Dean-Stark's apparatus. The resulting solution was washed with diluted hydrochloric acid and water, dried (MgSO4) and concentrated to obtain methyl 1,2-dihydro-6,7-dimethyl-4-(2-methylphenyl) -2-oxo-3-quinolinecarboxylate as crystals (5.3g, 82.6%}. Recrystallization from ethanol - chloroform gave colorless needles. mp 288°-289° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for an hour under ice-
  3. temperaturecooling
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto remove the solvent
  8. dissolutionThe oily product was dissolved in toluene (60 ml)
  9. additionDBU (0.3 g) was added to the solution
  10. temperatureThe solution was refluxed for 30 minutes with removal of water using Dean-Stark's apparatus
  11. washThe resulting solution was washed with diluted hydrochloric acid and water
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-56a69486a86645869ac3d0c6bbf2a380
Source dataset
uspto-grants-1993_06
Patent number
US05223513

Reaction notes

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