N-methyl-N-o-tolyl-acrylamide → HCID 86762702, compound

HRID 69035Notes

Reaction equation

HRID 69035 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[C:11](=[O:17])[CH:10]=[CH:9]2.[CH3:18][N:19]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30])[C:20](=[O:23])[CH:21]=[CH2:22]>C(O)C>[CH3:18][N:19]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30])[C:20](=[O:23])[CH2:21][CH2:22][NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[C:11](=[O:17])[CH:10]=[CH:9]2

Participants

4

Reactant 2

HCID 61987974N-methyl-N-o-tolyl-acrylamideHCID 669605486-(3-aminopropoxy)-1-methyl-1H-quinolin-2-one

Product 1

HCID 86762702HCID 86762702, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-(3-Amino-propoxy)-1-methyl-1H-quinolin-2-one (194 mg) was added to an ethanol solution (5 ml) of N-methyl-N-o-tolyl-acrylamide (146 mg). The mixture was stirred at room temperature overnight. The reaction mixture was condensed under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1→10:1). The purified product was condensed under reduced pressure to give the title compound (172.6 mg) as a colorless oil.

Workup

  1. customcondensed under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1→10:1)
  3. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-dfc04bc8f2504257a9ee2861d1a2d9cb
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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