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

HRID 1166058Notes

Reaction equation

HRID 1166058 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 (2.0 M) and extracted with dichloromethane. Combined organic extracts were washed with water, saturated aqueous sodium chloride solution and dried (MgSO4). The solvent was removed in vacuo and the residue was triturated with hexane/diethyl ether to give the product as a white solid (3.17 g, 92%); NMR δ(CD3SOCD3) 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 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with dichloromethane
  3. washCombined organic extracts were washed with water, saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customthe residue was triturated with hexane/diethyl ether

Sources & evidence

ORD record
ord-33e01c1a0e654952b0d4e1f313c31c28
Source dataset
uspto-grants-2003_09
Patent number
US06613760B1

Reaction notes

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