2-Methylbenzoyl chloride → HCID 68701513, compound

HRID 2352978Notes

Reaction equation

HRID 2352978 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][C:12]1[CH:13]=[C:14]([CH:27]=[CH:28][CH:29]=1)[C:15]([C:17]1[CH:25]=[C:24]2[C:20]([CH2:21][C:22](=[O:26])[NH:23]2)=[CH:19][CH:18]=1)=[O:16]>C1COCC1>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:11][C:12]1[CH:29]=[CH:28][CH:27]=[C:14]([C:15]([C:17]2[CH:25]=[C:24]3[C:20]([CH2:21][C:22](=[O:26])[NH:23]3)=[CH:19][CH:18]=2)=[O:16])[CH:13]=1)=[O:5]

Participants

4

Reactant 2

HCID 702762-Methylbenzoyl chlorideHCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 68701513HCID 68701513, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry flask was charged with 2-Methyl-benzoyl chloride (3.00 g, 19.41 mmol) and THF (200 mL). 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 4.895 g, 19.4 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux overnight. The reaction mixture was then allowed to cool to room temperature and filtered. The solid residue was washed with 0° C. THF (15 mL) and collected to afford the 2-Methyl-N-[3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-benzamide as a solid (5.174 g, 13.97 mmol, 72%).

Workup

  1. temperatureto reflux overnight
  2. filtrationfiltered
  3. washThe solid residue was washed with 0° C
  4. customTHF (15 mL) and collected

Sources & evidence

ORD record
ord-7f13aca2cafd43f5b3338848b2753c51
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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