Water → 4,4-Dimethyl-1,2,3,4-tetrahydroquinoline

HRID 1382914Notes

Reaction equation

HRID 1382914 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10](=O)[CH2:9]1.O.[OH-].[Na+]>CCOCC>[CH3:7][C:8]1([CH3:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 142099454,4-Dimethyl-3,4-dihydroquinolin-2(1H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 132194414,4-Dimethyl-1,2,3,4-tetrahydroquinolineYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a refluxing suspension of 10 g (0.26 mol) of lithium aluminum hydride in 100 ml of ether was added dropwise over a period of 1 hour a solution of 21.0 g (0.21 mol) of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinoline in 200 ml of ether-tetrahydrofuran (2:1, volume per volume). Refluxing was continued for 16 hours, and then to the cooled reaction mixture was added 50 ml of water and 50 ml of 10% sodium hydroxide. The aqueous phase was extracted with ether, and the combined ether extracts were dried (MgSO4) and evaporated in vacuo to give 17.2 g (89% yield) of the title compound as a clear oil.

Workup

  1. temperatureRefluxing
  2. customto the cooled reaction mixture
  3. extractionThe aqueous phase was extracted with ether
  4. dry with materialthe combined ether extracts were dried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-0640e922ac254ec0928e8ab3657e0598
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

Loading…