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

HRID 1973667Notes

Reaction equation

HRID 1973667 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)(=O)C>[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)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-aminocyclohex-2-enone (24.1g, 0.22m) and 3-ethoxy-2-methylacrolein (27.7g, 0.24m) in glacial acetic acid (55 ml.) was heated at reflux for 24 hours, cooled to 0° C and filtered. The solid (5g.) was recrystallised from ethanol as colourless needles m.p. 253° and identified di(2-methylprop-2-enalyl)amine.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. filtrationfiltered
  4. customThe solid (5g.) was recrystallised from ethanol as colourless needles m.p. 253°

Sources & evidence

ORD record
ord-749abd9c823b4f22a93a170c00fc7d70
Source dataset
uspto-grants-1976_12
Patent number
US03998831

Reaction notes

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