1,3-Cyclohexanedione → 3-(1,2,3,4-Tetrahydro-1-quinolinyl)-2-cyclohexen-1-one

HRID 727795Notes

Reaction equation

HRID 727795 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:11]1(=O)[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12]1>>[N:1]1([C:11]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 198250893-(1,2,3,4-Tetrahydro-1-quinolinyl)-2-cyclohexen-1-oneYield 15.6%

Procedure

A mixture of 1,2,3,4-tetrahydroquinoline (5 g) and 1,3-cyclohexanedione (4.21 g) was heated at ca. 150° for 5 h. The cooled reaction mixture was purified by FCC eluting with ethyl acetate to give the title compound (1.33 g) as an oil, t.l.c. (ethyl acetate) Rf 0.34.

Workup

  1. temperaturewas heated at ca. 150° for 5 h
  2. customThe cooled reaction mixture
  3. customwas purified by FCC
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-1460907208b4404892012a734759fd70
Source dataset
uspto-grants-1991_09
Patent number
US05045545

Reaction notes

Loading…