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

HRID 1861731Notes

Reaction equation

HRID 1861731 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]C1.[CH3:11][CH2:12]O.[CH3:14]COC(C)=O>[Pd]>[CH3:14][C:12]1([CH3:11])[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:1]1

Participants

5

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 52314021,2-Dihydroquinoline

Product 1

HCID 134958062,2-Dimethyl-1,2,3,4-tetrahydroquinolineYield 99%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a 1 L r.b., a solution of the dihydroquinoline (16.2 g) in 1:1 EtOH:EtOAc (300 mL) was treated with 10% Pd/C (1.05 g) and stirred under an atmosphere of hydrogen. The reaction was monitored by 1H NMR and was complete after 4 h. The reaction mixture was purged, filtered through a pad of Celite, and the pad was rinsed with EtOAc (200 mL). Concentration of the filtrate afforded 16.2 g (99%) of the tetrahydroquinoline as a pale yellow oil. 1H NMR (400 MHz, CDCl3) 6.98 (m, 2H), 6.60 (t, J=7.3, 1H), 6.44 (d, J=8.0, 1H), 2.77 (t, J=6.7, 2H), 1.70 (t, J=6.7, 2H), 1.21 (s, 6H).

Workup

  1. customThe reaction mixture was purged
  2. filtrationfiltered through a pad of Celite
  3. washthe pad was rinsed with EtOAc (200 mL)

Sources & evidence

ORD record
ord-d4762b0d39934aada657b3cab9c6a7a4
Source dataset
uspto-grants-2003_03
Patent number
US06534516B1

Reaction notes

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