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

HRID 1973669Notes

Reaction equation

HRID 1973669 reaction equation
C(O[CH:4]=[C:5]([CH3:8])[CH:6]=[O:7])C.[NH2:9][CH:10]=[C:11]([CH3:14])C=O.O.[C:16]1(C)[CH:21]=CC=C[CH:17]=1>>[CH3:14][C:11]1[CH:10]=[N:9][C:8]2[CH2:17][CH2:16][CH2:21][C:6](=[O:7])[C:5]=2[CH:4]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 5591983-Ethoxy-2-methyl-2-propenalHCID 3781742HCID 3781742, compound

Product 1

HCID 5951923-Methyl-7,8-dihydroquinolin-5(6H)-oneYield 4%

Procedure

A mixture of 3-aminocyclohex-2-enone (11.1 g. 0.1m) and 3-amino-2-methylacrolein (8.5 g. 0.1 m) in toluene (15 ml.) was heated at reflux below a Dean and Stark water separator for 48 hours. The solvent was removed and the residual oil distilled at 0.2 mm Hg to give the title compound as a colourless crystalline solid (0.5 g, 4%).

Workup

  1. temperaturewas heated
  2. customThe solvent was removed
  3. distillationthe residual oil distilled at 0.2 mm Hg

Sources & evidence

ORD record
ord-ad1a43e94222450190ac65f1feb3ee72
Source dataset
uspto-grants-1976_12
Patent number
US03998831

Reaction notes

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