ChemicalBook CAS DataBase List 4-HYDROXY-1H-INDOLE-3-CARBALDEHYDE

4-HYDROXY-1H-INDOLE-3-CARBALDEHYDE synthesis

5synthesis methods

Product Name:4-HYDROXY-1H-INDOLE-3-CARBALDEHYDE
CAS Number:81779-27-3
Molecular formula:C9H7NO2
Molecular Weight:161.16

2380-94-1
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81779-27-3
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Yield:-

Reaction Conditions:

with sodium hydroxide;trichlorophosphate in N-methyl-acetamide;water

Steps:

1 4-Hydroxyindole-3-carbaldehyde(1-1) (R7=R11=H)
4-Hydroxyindole-3-carbaldehyde(1-1) (R⁷=R¹¹=H) Phosphorous oxychloride 7.35 ml was added dropwise to dry dimethylformamide 15 ml under cooling in ice-methanol bath and the mixture was stirred for 15 min. Then, a solution of the 4-hydroxyindole 5.0 g in dry dimethylformamide 10 ml was added dropwise to the mixture under cooling in ice and the mixture was stirred for 2 h at room temperature. Water was added under cooling in ice to the mixture, which was made alkaline with a 30% aqueous sodium hydroxide solution and was stirred for 15 min. Then, the mixture was acidified to pH 4 with 5N-HCl and the precipitate was collected by filtration, washed with water and dried to give the titled compound 4.99 g as crude crystalline materials. Yield 82%. Crude crystalline materials are recrystallized from methanol to give yellow crystals m.p. 190-193 ØC. ¹H-NMR(DMSO-d₆): 6.54 (1H, dd, J = 8.1, 0.9 Hz), 6.95 (1H, dd, J = 8.1, 0.9 Hz), 7.13 (1H, t, J = 8.1 Hz), 8.37 (1H, s), 9.64 (1H, s), 10.54 (1H, br s), 12.35 (1H, br s).

References:

SHIONOGI & CO., LTD. EP1325909, 2003, A1

7042-71-9 Synthesis