Acetyl chloride → N-[4-(2-Oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-acetamide

HRID 2352805Notes

Reaction equation

HRID 2352805 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:23]=[CH:22][C:9]([C:10]([C:12]2[CH:20]=[C:19]3[C:15]([CH2:16][C:17](=[O:21])[NH:18]3)=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1>C1COCC1>[O:21]=[C:17]1[CH2:16][C:15]2[C:19](=[CH:20][C:12]([C:10]([C:9]3[CH:8]=[CH:7][C:6]([NH:5][C:1](=[O:3])[CH3:2])=[CH:23][CH:22]=3)=[O:11])=[CH:13][CH:14]=2)[NH:18]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 592564856-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 68700105N-[4-(2-Oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-acetamideYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry 100 mL flask was charged with acetyl chloride (0.408 g, 5.20 mmol) and THF (40 mL). 6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 15, 1.00 g, 3.96 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 room temperature reaction mixture was concentrated in vacuo. The brown solid residue was suspended in boiling EtOAc. The suspension was allowed to cool to room temperature before filtering to afford the N-[4-(2-Oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-acetamide as a tan solid (1.16 g, 3.94 mmol, 99%).

Workup

  1. temperatureto reflux for 3 h
  2. customThe room temperature reaction mixture
  3. concentrationwas concentrated in vacuo
  4. temperatureto cool to room temperature
  5. filtrationbefore filtering

Sources & evidence

ORD record
ord-df6bae780ed34ccba49d91b83ce60ee0
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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