Methyl 4-(chlorocarbonyl)benzoate → 5-(4-Methoxycarbonylbenzamido)-2-oxindole

HRID 24317

Reaction equation

HRID 24317 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH3:12][O:13][C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)=[O:15]>N1C=CC=CC=1>[CH3:12][O:13][C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6](=[O:11])[CH2:5]3)=[O:21])=[CH:18][CH:17]=1)=[O:15]

Participants

4

Reactant 2

HCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 27732135-Amino-2-oxindole

Product 1

HCID 232899625-(4-Methoxycarbonylbenzamido)-2-oxindoleYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 82.0 mg 5-amino-2-oxindole and 131.0 mg 4-methoxycarbonylbenzoyl chloride in pyridine was stirred at room temperature for 3 hr and poured into ice water. The precipitate was filtered, washed with water and dried in a vacuum oven to give 138.0 mg of 5-(4-methoxycarbonylbenzamido)-2oxindole (81% yield).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-1c489b6e3bdf42119d09d797f8064076
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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