3-Aminocyclohex-2-en-1-one → 3-Methyl-7,8-dihydroquinolin-5(6H)-one

HRID 1973665Notes

Reaction equation

HRID 1973665 reaction equation
[NH2:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.C(O[CH:12]=[C:13]([CH3:16])[CH:14]=O)C>C(O)C.O>[CH3:16][C:13]1[CH:12]=[N:1][C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]=2[CH:14]=1

Participants

4

Reactant 2

HCID 788923-Aminocyclohex-2-en-1-oneHCID 5591983-Ethoxy-2-methyl-2-propenal

Product 1

HCID 5951923-Methyl-7,8-dihydroquinolin-5(6H)-oneYield 48.4%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 3-aminocyclohex-2-enone (11.1 g., 0.1m) and 3-ethoxy-2-methylacrolein (11.4 g, 0.1m) was heated at 120° for 16 hours in a flask equipped for downward distillation. The ethanol-water distillate (6.5 ml.) was discarded and the residual oil distilled at 0.2 mm Hg to give 3-methyl-7,8-dihydro-5(6H)quinolone as a colourless oil b.p. 78°-80° (7.8 g, 48%) which solidified on standing and was recrystallized from 40- 60° petroleum ether as colourless needles m.p. 45°. Found: C, 74.81; H, 6.97; N, 8.91%. C10H11NO requires: C, 74.51; H, 6.88; N, 8.69%.

Workup

  1. temperaturewas heated at 120° for 16 hours in a flask
  2. customequipped for downward distillation
  3. distillationthe residual oil distilled at 0.2 mm Hg

Sources & evidence

ORD record
ord-313136fa6f9f4246bd6d91bbcf58b992
Source dataset
uspto-grants-1976_12
Patent number
US03998831

Reaction notes

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