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

HRID 74042Notes

Reaction equation

HRID 74042 reaction equation
[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=O)[CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]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-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (35 g, 0.2 mol) in THF (100 mL) was added dropwise to a suspension of LiAlH4 (18 g, 0.47 mol) in THF (200 mL) at 0° C. After addition, the mixture was stirred at room temperature for 30 min and then slowly heated to reflux for 1 h. The mixture was then cooled to 0° C. Water (18 mL) and NaOH solution (10%, 100 mL) were carefully added to quench the reaction. The solid was filtered off and the filtrate was concentrated to give 4,4-dimethyl-1,2,3,4-tetrahydro-quinoline.

Workup

  1. additionAfter addition
  2. temperatureslowly heated
  3. temperatureto reflux for 1 h
  4. temperatureThe mixture was then cooled to 0° C
  5. customto quench
  6. customthe reaction
  7. filtrationThe solid was filtered off
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a41cc1b247094bcc9be266bde6a90a03
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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