Benzoyl chloride → ethyl 3-benzamido-1H-indole-2-carboxylate

HRID 1728406Notes

Reaction equation

HRID 1728406 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(N(CC)CC)C.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[C:23]([NH:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 732887Ethyl 3-amino-1H-indole-2-carboxylate

Product 1

HCID 2157323ethyl 3-benzamido-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-Amino-2-carboethoxyindole (572 mg) and triethylamine (400 mg) in methylene chloride (100 mL) was added benzoyl chloride (450 mg). After 30 min at room temperature the reaction mixture was washed with 0.1N HCl, dried over magnesium sulfate and the solvent was removed in vacuo. The residue was triturated with ether to afford 3-Benzamido-2-carboethoxyindole as a white solid.

Workup

  1. washAfter 30 min at room temperature the reaction mixture was washed with 0.1N HCl
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-3e9acb9e8b4d418e9ce8d408cadacc6a
Source dataset
uspto-grants-1994_07
Patent number
US05326868

Reaction notes

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