Phthalic Anhydride → 2-[[(3-Methyl-1H-indol-1-yl)amino]carbonyl]benzoic acid

HRID 233122Notes

Reaction equation

HRID 233122 reaction equation
[NH2:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[CH:3]1.[C:12]1(=[O:22])[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12>C(Cl)(Cl)Cl>[CH3:11][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([NH:1][C:12]([C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=[O:16])=[O:22])[CH:3]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 124272923-Methyl-1H-indol-1-amine

Product 1

HCID 190369652-[[(3-Methyl-1H-indol-1-yl)amino]carbonyl]benzoic acidYield 105.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 2.0 g of N-amino-3-methylindole, 140 ml of dry chloroform and 2.74 g of phthalic anhydride was stirred at reflux for 4 hours. The suspension was allowed to cool to room temperature, concentrated to approximately 50 ml, filtered and the residue washed with chloroform to provide 4.25 g of a white solid. Recrystallization from ethyl acetate provided 3.18 g (79.0%) of 2-[[(3-methyl(indol-1-yl)amino]carbonyl]benzoic acid, m.p. 191°-193° C.

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationconcentrated to approximately 50 ml
  3. filtrationfiltered
  4. washthe residue washed with chloroform

Sources & evidence

ORD record
ord-e49f0e776a1c43d9989b2c5fb673821c
Source dataset
uspto-grants-1997_01
Patent number
US05591866

Reaction notes

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