Ethyl 7-(benzyloxy)-4-formyl-1H-indole-2-carboxylate → 7-(Benzyloxy)-4-formyl-1H-indole-2-carboxylic acid

HRID 1762962Notes

Reaction equation

HRID 1762962 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([CH:15]=[O:16])[CH:11]=[CH:10][C:9]=2[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:5])C>[OH-].[Na+].C(O)C>[CH2:18]([O:17][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[C:13]2[C:8]=1[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 13243484Ethyl 7-(benzyloxy)-4-formyl-1H-indole-2-carboxylate

Product 1

HCID 132434857-(Benzyloxy)-4-formyl-1H-indole-2-carboxylic acidYield 107.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

2.26 g of 7-benzyloxy-4-formylindole-2-carboxylic acid ethyl ester is heated in a mixture of 15 ml of 1N sodium hydroxide solution and 15 ml of ethanol for one hour to 100° C. The ethanol is then distilled off under vacuum, the mixture is acidified with 10% hydrochloric acid and the precipitate is vacuum-filtered. The product is recrystallized from glacial acetic acid, thus obtaining 2.22 g of 7-benzyloxy-4-formylindole-2-carboxylic acid, mp 207° C.

Workup

  1. distillationThe ethanol is then distilled off under vacuum
  2. filtrationthe precipitate is vacuum-filtered
  3. customThe product is recrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-cef7baf402e546d8b689c04c55db1920
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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