1,3-Cyclohexanedione → HCID 178479633, compound

HRID 1292940Notes

Reaction equation

HRID 1292940 reaction equation
[ClH:1].[N:2]1([NH2:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[C:13]1(=O)[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH2:14]1>CC(O)=O.O>[ClH:1].[N:2]1([N:12]=[C:13]2[CH2:18][CH2:17][CH2:16][C:15]([OH:19])=[CH:14]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 225037343,4-Dihydro-2H-quinolin-1-ylamine hydrochloride

Product 1

HCID 178479633HCID 178479633, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

3,4-Dihydro-1(2H)-quinolinamine hydrochloride (5.0 g, 27 mmol) and 1,3-cyclohexanedione (3.1 g, 27 mmol) was mixed in AcOH (4.3 mL) and H2O (4.3 mL). The mixture was heated at 40° C. for 10 min until dissolved completely. The mixture was then concentrated to dryness. The residue was washed with acetonitrile then filtered to yield 3-(3,4-dihydro-1(2H)-quinolinylimino)-1-cyclohexen-1-ol hydrochloride (5.2 g, 69%) as a yellow solid.

Workup

  1. dissolutionuntil dissolved completely
  2. concentrationThe mixture was then concentrated to dryness
  3. washThe residue was washed with acetonitrile
  4. filtrationthen filtered

Sources & evidence

ORD record
ord-881da643bf084857a3643fcc588cf80c
Source dataset
uspto-grants-2007_07
Patent number
US07238690B2

Reaction notes

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