Water → 2-Aminocarbonylamino-6-formylindole-3-carboxamide

HRID 216637Notes

Reaction equation

HRID 216637 reaction equation
I(C1C=CC=CC=1C(O)=O)(=O)=O.[NH2:13][C:14]([NH:16][C:17]1[NH:18][C:19]2[C:24]([C:25]=1[C:26]([NH2:28])=[O:27])=[CH:23][CH:22]=[C:21]([CH2:29][OH:30])[CH:20]=2)=[O:15].O>CS(C)=O>[NH2:13][C:14]([NH:16][C:17]1[NH:18][C:19]2[C:24]([C:25]=1[C:26]([NH2:28])=[O:27])=[CH:23][CH:22]=[C:21]([CH:29]=[O:30])[CH:20]=2)=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 1087942-Iodoxybenzoic acidHCID 249894282-Aminocarbonylamino-6-hydroxymethylindole-3-carboxamide2×

Product 1

HCID 866390762-Aminocarbonylamino-6-formylindole-3-carboxamideYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Iodoxybenzoic acid (1.8 g, 6.4 mmol) was added to a solution of 2-aminocarbonylamino-6-hydroxymethylindole-3-carboxamide (Compound 16-1, 1.4 g, 5.8 mmol) in dimethyl sulfoxide (100 mL), and the mixture was stirred at room temperature for 30 minutes. Water (100 mL) was added to the reaction mixture under ice-cooling, and the precipitated solid was separated by filtration. The resultant solid was washed with 0.25 N sodium hydroxide aqueous solution-(5 mL) and water (5 mL) and dried under reduced pressure to give the title compound (1.1 g) as a brown solid (yield 74%).

Workup

  1. temperaturecooling
  2. customthe precipitated solid was separated by filtration
  3. washThe resultant solid was washed with 0.25 N sodium hydroxide aqueous solution-(5 mL) and water (5 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-8477c53fb5cc4ea39fdcd5c87122d842
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

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