ChemicalBook CAS DataBase List Ethyl 5-hydroxyindole-2-carboxylate

Ethyl 5-hydroxyindole-2-carboxylate synthesis

6synthesis methods

Product Name:Ethyl 5-hydroxyindole-2-carboxylate
CAS Number:24985-85-1
Molecular formula:C11H11NO3
Molecular Weight:205.21

37033-95-7
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24985-85-1
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Yield:24985-85-1 99%

Reaction Conditions:

with hydrogen;10% palladium on activated carbon in ethanol; for 20 h;

Steps:

1.c Scheme 1; EXAMPLE 1; Preparation of 5-(2-Chloro-5-hydroxybenzyloxy)-1-[(2-thiophen-3-yl)ethyl]-1H-indole-2-carboxylic Acid; c) 5-Hydroxyindole-2-carboxylic Acid Ethyl Ester

A solution of 5-benzyloxyindole-2-carboxylic acid ethyl ester (10 g, 34 mmol) in ethanol (250 mL) was treated with 10% Pd/C and hydrogenated under atmospheric pressure (double-walled balloon) for 20 h. The reaction mixture was diluted with EtOAc and filtered through Celite. Evaporation of the filtrate in vacuo gave the title compound as a tan solid (7 g, 99%). ¹H NMR (400 MHz, CDCl₃) δ 8.86 (br s, 1H), 7.29 (d, J=8.80 Hz, 1H), 7.11 (s, 1H), 7.06 (s, 1H), 6.94 (d, J=8.70 Hz, 1H), 4.83 (br s, 1H), 4.42 (q, J=7.09 Hz, 2H), 1.41 (t, J=7.08 Hz, 3H).

References:

US6670388,2003,B1 Location in patent:Page column 6