Ammonium formate → N-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide

HRID 1352502Notes

Reaction equation

HRID 1352502 reaction equation
C([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([N:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](=[O:21])[CH3:20])[CH2:10][CH:9]1[CH3:28])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:28][CH:9]1[CH2:10][CH:11]([N:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](=[O:21])[CH3:20])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:8]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22935741N-(1-benzyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide

Product 1

HCID 2837129N-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamideYield 105.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-(1-benzyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide (50 mg) and ammonium formate (85 mg) and palladium on activated carbon 10% in ethanol (2 ml) were warmed to reflux for 1 hour. The solution was filtered on celite and the solvent was removed to afford N-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide (40 mg).

Workup

  1. temperatureto reflux for 1 hour
  2. filtrationThe solution was filtered on celite
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-3842db412c6148bc97f58595c698df17
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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