Ethanol → 2,2-Dimethyl-1,2,3,4-tetrahydroquinolin-7-amine

HRID 850346Notes

Reaction equation

HRID 850346 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([N+:12]([O-])=O)=[CH:7][CH:8]=2)[NH:3]1.CCO>[Pd].CCOC(C)=O>[NH2:12][C:6]1[CH:5]=[C:4]2[C:9]([CH2:10][CH2:11][C:2]([CH3:15])([CH3:1])[NH:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 105124651,2,3,4-Tetrahydro-2,2-dimethyl-7-nitroquinoline

Product 1

HCID 105352872,2-Dimethyl-1,2,3,4-tetrahydroquinolin-7-amineYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a 200-mL r.b. flask, a solution of 1,2,3,4-tetrahydro-2,2-dimethyl-7-nitroquinoline (1.00 g, 4.84 mmol) in 1:1 EtOH:EtOAc (40 mL) was treated with 10% Pd/C (0.20 g). The reaction mixture was de-gassed and fitted with a balloon of H2. The reaction mixture was stirred for 6 h, de-gassed, and filtered through a pad of Celite. The pad was rinsed with EtOAc (300 mL). The filtrate was concentrated to afford 0.85 g (99%) of the crude aniline as a reddish oil. Data for 7-amino-1,2,3,4-tetrahydro-2,2-dimethylquinoline: 1H NMR (400 MHz, CDCl3) 6.77 (d, J=7.9, 1H), 6.00 (dd, J=7.9, 2.2, 1H), 5.81 (d, J=2.2, 1H), 3.47 (bs, 1H), 3.40 (bs, 2H), 2.66 (t, J=6.7, 2H), 1.65 (t, J=6.7, 2H), 1.18 (s, 6H).

Workup

  1. customThe reaction mixture was de-gassed
  2. customfitted with a balloon of H2
  3. customde-gassed
  4. filtrationfiltered through a pad of Celite
  5. washThe pad was rinsed with EtOAc (300 mL)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ac82240be7af48e1b0ca291eeb859166
Source dataset
uspto-grants-2000_01
Patent number
US06017924

Reaction notes

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