3-Amino-5,5-dimethyl-2-cyclohexen-1-one → 5,6,7,8-Tetrahydro-3,7,7-trimethylquinoline-5-one

HRID 1973672Notes

Reaction equation

HRID 1973672 reaction equation
[NH2:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=1.[CH3:11][C:12](=[CH:15]OCC)[CH:13]=O>>[CH3:15][C:12]1[CH:11]=[N:1][C:2]2[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[C:3]=2[CH:13]=1

Participants

3

Reactant 2

HCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 5591983-Ethoxy-2-methyl-2-propenal

Product 1

HCID 41751925,6,7,8-Tetrahydro-3,7,7-trimethylquinoline-5-oneYield 60.8%

Procedure

A mixture of 3-amino-5,5-dimethylcyclohex-2-enone (27.8g., 0.2 mol.) and 2-methyl-3-ethoxyacrolein (22.8 g., 0.2 mol.), in an apparatus equipped for downward distillation, was heated in an oil bath at 120° until the theoretical quantity of distillate was collected (13 ml.) The cooled residue was diluted with 2N HCl (50 ml.), extracted with ethyl acetate (3 × 50 ml.) and the combined extracts discarded. The aqueous solution was adjusted to pH 9.0 with sodium carbonate and extracted with ethyl acetate (3 × 50 ml.). The combined extracts were dried (MgSO4) and the solvent removed in vacuo and the residual oil distilled to give the title compound as a colourless oil (23 g., 53%) b.p. 83°/0.2 mm Hg. (RT = 2 min., 2% OV17, T=150° C).

Workup

  1. customin an apparatus equipped for downward distillation
  2. temperaturewas heated in an oil bath at 120° until the theoretical quantity of distillate
  3. customwas collected (13 ml.) The cooled residue
  4. additionwas diluted with 2N HCl (50 ml.)
  5. extractionextracted with ethyl acetate (3 × 50 ml.)
  6. extractionextracted with ethyl acetate (3 × 50 ml.)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customthe solvent removed in vacuo
  9. distillationthe residual oil distilled

Sources & evidence

ORD record
ord-3cc924f443b945d093a5403c0c48221f
Source dataset
uspto-grants-1976_12
Patent number
US03998831

Reaction notes

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