Ammonia → 3-Benzamidoindole-2-carboxamide

HRID 1728407

Reaction equation

HRID 1728407 reaction equation
[C:1]([NH:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:19]([O:21]CC)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[NH3:29]>C(O)(C)C>[C:1]([NH:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:19]([NH2:29])=[O:21])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 2157323ethyl 3-benzamido-1H-indole-2-carboxylate

Product 1

HCID 152847253-Benzamidoindole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-Benzamido-2-carboethoxyindole (3.0 g) and phosphorous oxychloride (20 mL) was refluxed for 30 min. The reaction mixture was concentrated in vacuo and the residue was triturated with ether to afford a white solid. This solid was treated with 40 mL of isopropanol which had been previously saturated with ammonia and heated in a sealed tube at 120° C. for 40 min. The reaction mixture was again concentrated in vacuo and the residue was triturated with ether to afford 3-Benzamido-indole-2-carboxamide as a white solid.

Workup

  1. temperaturewas refluxed for 30 min
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was triturated with ether
  4. customto afford a white solid
  5. concentrationThe reaction mixture was again concentrated in vacuo
  6. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-d64c1a773ba246a289c1fd799e10843f
Source dataset
uspto-grants-1994_07
Patent number
US05326868

Linked notes

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