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51991-39-0

1H-Indole-2-carboxylic acid, 5-hydroxy-, methyl ester synthesis

10synthesis methods
-

Yield:51991-39-0 100%

Reaction Conditions:

with hydrogenchloride for 48 h;Heating / reflux;

Steps:

4; 5

Methyl 5-hydroxy-2-indolecarboxylate (1); Dissolved 3.50 g 5-hydroxy-2-indolecarboxylic acid in anh. MeOH presaturated with HCl gas. Refluxed for 48 hours. Concentrated in vacuo and triturated with AcCN×3 to remove residual acid. Filtered through silica plug with EtOAc to remove baseline contamination. Recovered 4.32 g (quant. yield) TLC Rf=0.78 (EtOAc) 1H NMR (DMSO-d6): 3.82 (s, 3H), 6.78 (d, J=8.8 Hz, 1H), 6.88 (s, 1H), 6.93 (s, 1H), 7.23 (d, J=8.8 Hz, 1H), 8.90 (s, 1H) 11.62 (s, 1H) FAB(+) MS m/e 191.9 (M+1)

References:

US2008/4241,2008,A1 Location in patent:Page/Page column 136-138