Sulfuric Acid → HCID 22627455, compound

HRID 278128Notes

Reaction equation

HRID 278128 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([NH2:16])=[O:15])[CH:12]=2)[C:7]([CH:17]=[O:18])=[CH:6]1.S(=O)(=O)(O)[OH:24]>CN(C)C=O>[C:14]([C:11]1[CH:12]=[C:13]2[C:8]([C:7]([C:17]([OH:24])=[O:18])=[CH:6][N:5]2[CH2:4][C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]=2[Cl:1])=[CH:9][CH:10]=1)(=[O:15])[NH2:16]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 22627139HCID 22627139, compound

Product 1

HCID 22627455HCID 22627455, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 1-(2-chlorobenzyl)-3-formylindole-6-carboxamide (47 mg) in dimethylformamide (1.6 ml) was added chromic anhydride (125 mg) and sulfuric acid (0.05 ml), and the mixture was stirred at 20° C. for 5 hours. The resulting mixture was evaporated in vacuo and the residue was chromatographed on silica gel eluting with a mixture of chloroform and methanol (9:1) to give 6-carbamoyl-1-(2-chlorobenzyl)indole-3-carboxylic acid (8.3 mg) as a solid.

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel eluting with a mixture of chloroform and methanol (9:1)

Sources & evidence

ORD record
ord-e996044040e0460086c7cd63938c9c03
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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