Triethylamine → 3-Methyl-7,8-dihydroquinolin-5(6H)-one

HRID 372683Notes

Reaction equation

HRID 372683 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.[NH2:9][CH:10]=[C:11]([CH3:14])[CH:12]=O.C(N(CC)CC)C>Cl.C([O-])(=O)C.[NH2+]1CCCCC1>[CH3:14][C:11]1[CH:10]=[N:9][C:3]2[CH2:4][CH2:5][CH2:6][C:1](=[O:8])[C:2]=2[CH:12]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 3781742HCID 3781742, compound

Product 1

HCID 5951923-Methyl-7,8-dihydroquinolin-5(6H)-oneYield 52.7%

Reagents, catalysts & solvents 2

HCID 3014295Piperidinium acetateCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of cyclohexane-1,3-dione (22.4 g., 0.2 mol.), 3-amino-2-methylacrolein (17 g., 0.2 mol.), triethylamine (10 ml.) and piperidinium acetate (0.25 g.) was heated with stirring in an oil bath at 120° C for 24 hours. The cooled reaction mixture was dissolved in 2N HCl (50 ml.) and extracted with ethyl acetate (3 × 50 ml.) and the organic extracts discarded. The aqueous solution was adjusted to pH 10 with sodium carbonate and extracted with chloroform (3 × 50 ml.). The combined extracts were dried (MgSO4) and the solvent removed in vacuo. The residual oil was distilled to give the title compound as a colorless oil (17 g., 52%) b.p. 79°/0.2 mm Hg which solidified.

Workup

  1. temperaturewas heated
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate (3 × 50 ml.)
  4. extractionextracted with chloroform (3 × 50 ml.)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent removed in vacuo
  7. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-e1631ca4e14647c4864958fe7bc685f0
Source dataset
uspto-grants-1978_05
Patent number
US04092317

Reaction notes

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