Acetyl chloride → N-[3-(2-Oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide

HRID 640824Notes

Reaction equation

HRID 640824 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[CH2:14]2)=[O:10]>C1COCC1>[O:20]=[C:15]1[CH2:14][C:13]2[C:17](=[CH:18][CH:19]=[C:11]([C:9]([C:8]3[CH:7]=[C:6]([NH:5][C:1](=[O:3])[CH3:2])[CH:23]=[CH:22][CH:21]=3)=[O:10])[CH:12]=2)[NH:16]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 644240015-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 68698490N-[3-(2-Oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamideYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry 25 mL flask was charged with acetyl chloride (0.273 g, 3.48 mmol) and THF (5 mL). 5-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 1, 0.675 g, 2.67 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 3 h. The reaction mixture was then allowed to cool to room temperature. The tan precipitate was filtered to afford N-[3-(2-Oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide (0.478 g, 1.48 mmol, 61%).

Workup

  1. temperatureto reflux for 3 h
  2. filtrationThe tan precipitate was filtered

Sources & evidence

ORD record
ord-a350533e86ea43e1bcf0ced532a2586f
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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