Acetamide, N-3-quinolinyl- → N-(1,2,3,4-tetrahydroquinolin-3-yl)acetamide

HRID 863247Notes

Reaction equation

HRID 863247 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:3])[CH3:2].C(OCC)(=O)C.CCCCCC>C(O)C.[Pd]>[CH3:2][C:1]([NH:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH2:6]1)=[O:3]

Participants

5

Reactant 2

HCID 79448Acetamide, N-3-quinolinyl-HCID 21226206Ethyl acetate hexane

Product 1

HCID 19697545N-(1,2,3,4-tetrahydroquinolin-3-yl)acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

300 mg of the 3-(acetylamino)quinoline (Rf (D)=0.43) obtained by a single recrystallization from ethyl acetate/hexane are hydrogenated in 10 ml of ethanol in the presence of 60 mg of palladium-on-charcoal (10% of Pd) at 50° C. under normal pressure for 20 h. After the reaction mixture has been filtered over Celite® 545 and the crude product has been purified by chromatography over 25 g of silica gel (mobile phase P), 3(R,S)-methylcarbonylamino-1,2,3,4-tetrahydroquinoline is obtained: Rf (P)=0.49; MS: (M)+ =190.

Workup

  1. filtrationAfter the reaction mixture has been filtered over Celite® 545
  2. customthe crude product has been purified by chromatography over 25 g of silica gel (mobile phase P)

Sources & evidence

ORD record
ord-b6c27f62036443d4b365dedab9fc3976
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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