Acetyl chloride → N-[4-(2-Oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide

HRID 640835Notes

Reaction equation

HRID 640835 reaction equation
C(Cl)(=O)C.OC=[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]4N(CC)N=C(C)C=4)=[O:26])=[CH:20][CH:19]=3)=[O:17])[CH:14]=2)[NH:9][C:8]1=[O:35]>C1COCC1>[O:35]=[C:8]1[CH2:7][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:26])[CH3:27])=[CH:20][CH:19]=3)=[O:17])[CH:14]=2)[NH:9]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178463080HCID 178463080, compound

Product 1

HCID 68696666N-[4-(2-Oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamideYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry 25 mL flask was charged with acetyl chloride (0.209 g, 2.67 mmol) and THF (10 mL). 5-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 7, 0.512 g, 2.06 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 precipitate that formed was filtered and washed with THF affording N-[4-(2-Oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide (0.503 g, 1.56 mmol, 83%).

Workup

  1. temperatureto reflux for 3 h
  2. customThe precipitate that formed
  3. filtrationwas filtered
  4. washwashed with THF

Sources & evidence

ORD record
ord-c0e5191a46794f42bd20dfa9313081f3
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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