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

HRID 372684Notes

Reaction equation

HRID 372684 reaction equation
[CH3:1][C:2]1(C)[CH2:9][C:7](=O)[CH2:6][C:4](=[O:5])[CH2:3]1.C([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])C.[C:18]([O-])(=O)C.[NH4+]>Cl>[CH3:18][C:17]1[CH:16]=[N:13][C:14]2[CH2:15][C:2]([CH3:9])([CH3:1])[CH2:3][C:4](=[O:5])[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31358DimedoneHCID 517165Ammonium Acetate

Product 1

HCID 41751925,6,7,8-Tetrahydro-3,7,7-trimethylquinoline-5-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-amino-2-methacrolein (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 bicarbonate 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 colorless 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-610b9cdbf5644351a94c56e28cd332f0
Source dataset
uspto-grants-1978_05
Patent number
US04092317

Reaction notes

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