Triethylamine → 5,6,7,8-Tetrahydro-3,7,7-trimethylquinoline-5-one

HRID 1973671Notes

Reaction equation

HRID 1973671 reaction equation
[NH2:1][CH:2]=[C:3]([CH3:6])[CH:4]=O.[CH3:7][C:8]1([CH3:16])[CH2:15][C:13](=O)[CH2:12][C:10](=[O:11])[CH2:9]1.C(N(CC)CC)C>Cl.C([O-])(=O)C.[NH4+]>[CH3:6][C:3]1[CH:2]=[N:1][C:13]2[CH2:15][C:8]([CH3:7])([CH3:16])[CH2:9][C:10](=[O:11])[C:12]=2[CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31358DimedoneHCID 3781742HCID 3781742, compound

Product 1

HCID 41751925,6,7,8-Tetrahydro-3,7,7-trimethylquinoline-5-oneYield 41.2%

Reagents, catalysts & solvents 2

HCID 517165Ammonium AcetateCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-amino-2-methylacrolein (8.5 g., 0.1 mol.) and dimedone (14 g., 0.1 mol.) was treated with triethylamine (5 ml.) and ammonium acetate (0.1 g.) and heated in an oil bath at 120° C with stirring for 20 hours. The cooled reaction mixture was diluted with 2N HCl (50 ml.) and extracted with ethyl acetate (2 × 50 ml.) and the extracts discarded. The aqueous solution was adjusted to pH 10.0 with sodium carbonate and extracted with ethyl acetate (3 × 50 ml.). The combined extracts were dried (MgSO4 and the solvent removed to give a residual oil which was distilled to give the title compound as a colourless oil (7.8 g., 40%) b.p. 80°/0.2 mm Hg. (RT = 2 min. 2% OV17, T=150°).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate (2 × 50 ml.)
  3. extractionextracted with ethyl acetate (3 × 50 ml.)
  4. dry with materialThe combined extracts were dried (MgSO4
  5. customthe solvent removed
  6. customto give a residual oil which
  7. distillationwas distilled

Sources & evidence

ORD record
ord-2eb50403f1ea4f37991e7a31d3444d40
Source dataset
uspto-grants-1976_12
Patent number
US03998831

Reaction notes

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