Sodium ethoxide → Ethyl N-(3,4-dichlorobenzyl)-5-hydroxyindole-2-carboxylate

HRID 1582634Notes

Reaction equation

HRID 1582634 reaction equation
[O-]CC.[Na+].C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[C:13]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:12]2)(=O)C>C(O)C>[Cl:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[Cl:25])[CH2:18][N:14]1[C:15]2[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=2)[CH:12]=[C:13]1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 11463881Ethyl 5-acetoxy-N-(3,4-dichlorobenzyl)indole-2-carboxylate

Product 1

HCID 11233838Ethyl N-(3,4-dichlorobenzyl)-5-hydroxyindole-2-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (1.86 g) was added to a stirred solution of ethyl 5-acetoxy-N-(3,4-dichlorobenzyl)indole-2-carboxylate (5.55 g) in ethanol (50 ml) under an atmosphere of argon. The reaction was stirred at room temperature for 2 hours, then concentrated in vacuo and the residue acidified with aqueous hydrochloric acid (2 M) and extracted with dichloromethane. Combined organic extracts were washed with water, saturated aqueous sodium chloride solution and dried. The solvent was removed in vacuo and the residue was triturated with hexane/diethyl ether to yield the product as a white solid (3.17 g, 92%). NMR: δ 1.26 (t, 3H), 4.25 (q, 2H), 5.75 (s, 2H), 6.81-6.91 (m, 2H), 6.98 (d, 1H), 7.19 (s, 1H), 7.29 (d, 1H), 7.38 (d, 1H) 7.50 (d, 1H), 9.06 (s, 1H); m/z 364 (M+H+).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with dichloromethane
  3. washCombined organic extracts were washed with water, saturated aqueous sodium chloride solution
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customthe residue was triturated with hexane/diethyl ether

Sources & evidence

ORD record
ord-fc5a8dd35f674151a30900995a14691a
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

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