HCID 68924959, compound → HCID 21100554, compound

HRID 1786086Notes

Reaction equation

HRID 1786086 reaction equation
C(OC([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]([N:21]([C:25](=[O:27])[CH3:26])[CH:22]2[CH2:24][CH2:23]2)[CH2:13][CH:12]1[CH3:28])=O)C1C=CC=CC=1>CO.[Pd]>[CH:22]1([N:21]([CH:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:11][CH:12]([CH3:28])[CH2:13]2)[C:25](=[O:27])[CH3:26])[CH2:23][CH2:24]1

Participants

4

Reactant 1

HCID 68924959HCID 68924959, compound

Product 1

HCID 21100554HCID 21100554, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl-4-[acetyl(cyclopropyl)amino]-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate was dissolved in MeOH and a catalytic amount of Palladium on Carbon (10%) was added. The round bottom flask in which resided the resulting solution was evacuated and backfilled with hydrogen. The reaction was stirred under the hydrogen atmosphere overnight. The mixture was carefully filtered through a Celite® plug and concentrated to afford crude product. The crude residue was purified by silica gel chromatography (hexanes-ethyl acetate system) to afford N-cyclopropyl-N-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)acetamide.

Workup

  1. customwas evacuated
  2. filtrationThe mixture was carefully filtered through a Celite® plug
  3. concentrationconcentrated
  4. customto afford crude product
  5. customThe crude residue was purified by silica gel chromatography (hexanes-ethyl acetate system)

Sources & evidence

ORD record
ord-96a1d62622154a9db43cd54b2b12573a
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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