2,2-Diethyl-1,2-dihydroquinoline → 2,2-Diethyl-1,2,3,4-tetrahydroquinoline

HRID 850355Notes

Reaction equation

HRID 850355 reaction equation
CC1(C)CCC2C(=CC=CC=2)N1.[CH2:13]([C:15]1([CH2:25][CH3:26])[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16]1)[CH3:14]>CCOC(C)=O.[Pd]>[CH2:25]([C:15]1([CH2:13][CH3:14])[CH2:24][CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16]1)[CH3:26]

Participants

5

Reactant 2

HCID 104878352,2-Diethyl-1,2-dihydroquinolineHCID 134958062,2-Dimethyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 186212832,2-Diethyl-1,2,3,4-tetrahydroquinolineYield 70.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

This compound was prepared in a manner similar to that described for 1,2,3,4-tetrahydro-2,2-dimethylquinoline (structure 18 of Scheme III, where R1 =R2 =Me) from 2,2-diethyl-1,2-dihydroquinoline (1.46 g, 7.80 mmol) and 10% Pd/C (146 mg, 10% by weight) in EtOAc (18.7 mL) to afford 1.04 g (70%) 2,2-diethyl-1,2,3,4-tetrahydroquinoline after flash chromatography (hexanes:EtOAc, 97:3). Data for 2,2-diethyl-1,2,3,4-tetrahydroquinoline: Rf 0.43 (24:1 hexanes:ethyl acetate); 1H NMR (400 MHz, CDCl3) 6.90-7.00 (m, 2H), 6.57 (td, J=7.3, 1.0, 1H), 6.46 (dd, J=8.4, 1.0, 1H), 3.63 (broad s, 1H), 2.72 (t, J=6.7, 2H), 1.69 (t, J=6.7,2H), 1.38-1.53 (m, 4H), 0.86 (t, J=7.4,6H).

Workup

  1. customThis compound was prepared in a manner similar to

Sources & evidence

ORD record
ord-71c99075b5fb422fa22c484e557a8641
Source dataset
uspto-grants-2000_01
Patent number
US06017924

Reaction notes

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