HCID 21961374, compound → 1-Ethyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-7-amine

HRID 2247226Notes

Reaction equation

HRID 2247226 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=2)[C:6]([CH3:17])([CH3:16])[CH2:5][CH2:4]1)[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[C:6]([CH3:16])([CH3:17])[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 21961374HCID 21961374, compound

Product 1

HCID 219614881-Ethyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-7-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 1-ethyl-4,4-dimethyl-7-nitro-1,2,3,4-tetrahydro-quinoline (0.28 g) and Pd/C (0.060 g, 10% wt) in 10 ml of EtOAc was placed under H2 which was provided by a balloon and stirred at RT overnight. Then the mixture was filtered through Celite®, condensed, and the residue was purified by flash column chromatography (2% of EtOAc in CH2Cl2). The titled compound was obtained as a pink oil. MS(ES+): 204.8 (M+H)+. Calc'd for C11H16N—204.31.

Workup

  1. customwas provided by a balloon
  2. filtrationThen the mixture was filtered through Celite®, condensed
  3. customthe residue was purified by flash column chromatography (2% of EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-aad16a98d2994175b74dbc633b12b88d
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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