Triethylamine → N-(4-Methylphenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide

HRID 450105Notes

Reaction equation

HRID 450105 reaction equation
[O:1]=[C:2]([C:6]1[N:14]2[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]2)=[CH:8][C:7]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3](Cl)=[O:4].C([N:23]([CH2:26][CH3:27])CC)C>ClCCl>[O:1]=[C:2]([C:6]1[N:14]2[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]2)=[CH:8][C:7]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]([NH:23][C:26]1[CH:27]=[CH:8][C:7]([CH3:15])=[CH:6][CH:2]=1)=[O:4]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 50082602-oxo-2-(2-phenylindolizin-3-yl)acetyl Chloride

Product 1

HCID 2905584N-(4-Methylphenyl)-alpha-oxo-2-phenyl-3-indolizineacetamideYield 128.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of oxo-(2-phenyl-indolizin-3-yl)-acetyl chloride (0.5 g, 1.76 mmol) and p-toludine (0.21 g, 1.94 mmol) in dichloromethane (10 ml) was added triethylamine (0.5 ml, 3.52 mmol). The reaction mixture was stirred at room temperature for 1 hr. The solvent was evaporated under vacuum. Column chromatography on silica gel afforded 2-oxo-2-(2-phenyl-indolizin-3-yl)-N-p-tolyl-acetamide (0.4 g, 65%).

Workup

  1. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-fe7cede7575e49ac89a2acf9f104d0a7
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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