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

HRID 1973668Notes

Reaction equation

HRID 1973668 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.C(O[CH:12]=[C:13]([CH3:16])[CH:14]=O)C.C([N:19](CC)CC)C>CCOCC.C([O-])(=O)C.[NH4+]>[CH3:14][C:13]1[CH:12]=[N:19][C:3]2[CH2:4][CH2:5][CH2:6][C:1](=[O:8])[C:2]=2[CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 5591983-Ethoxy-2-methyl-2-propenal

Product 1

HCID 5951923-Methyl-7,8-dihydroquinolin-5(6H)-oneYield 48%

Reagents, catalysts & solvents 2

HCID 517165Ammonium AcetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of cyclohexane-1,3-dione (11.2 g. 0.1 m), 3-amino-2-methylacrolein (8.5 g. 0.1m) triethylamine (5 ml.) and ammonium acetate (100 mg) were heated with stirring at 120° in an oil bath for 12 hours. The cooled reaction mixture was diluted with ether (50 ml.) and the solution washed with 2N HCl (3 × 15 ml.) The combined washings were adjusted to pH 9.0 with sodium carbonate and extracted with ether (3 × 50 ml.) The combined extracts were dried, evaporated in vacuo and the residual oil distilled at 0.2 mm Hg to give the title compound as a colourless crystalline solid b.p. 80° (7.5 g. 48%).

Workup

  1. temperaturewere heated
  2. customThe cooled reaction mixture
  3. washthe solution washed with 2N HCl (3 × 15 ml.) The combined washings
  4. extractionextracted with ether (3 × 50 ml.) The combined extracts
  5. customwere dried
  6. customevaporated in vacuo
  7. distillationthe residual oil distilled at 0.2 mm Hg

Sources & evidence

ORD record
ord-51b4b626a0284eb0a20fab8c3fa7139f
Source dataset
uspto-grants-1976_12
Patent number
US03998831

Reaction notes

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