ChemicalBook CAS DataBase List ETHYL 6-FORMYLAMINO-5-METHOXYINDOLE-2-CARBOXYLATE

ETHYL 6-FORMYLAMINO-5-METHOXYINDOLE-2-CARBOXYLATE synthesis

5synthesis methods

Product Name:ETHYL 6-FORMYLAMINO-5-METHOXYINDOLE-2-CARBOXYLATE
CAS Number:119825-27-3
Molecular formula:C13H14N2O4
Molecular Weight:262.26

107575-59-7 Synthesis

ETHYL PYRUVATE-3-FORMYLAMINO-4-METHOXYPHENYLHYDRAZONE

107575-59-7
10 suppliers
$405.00/50mg

ETHYL 6-FORMYLAMINO-5-METHOXYINDOLE-2-CARBOXYLATE

119825-27-3
13 suppliers
inquiry

Yield:119825-27-3 75.2%

Reaction Conditions:

with formic acid at 80;

Steps:

1.E; e

Ethyl 2-[(3-formylamino-4-memoxypheiiyl)hydrazono)propionate (6) (425.0 g, 1.53 mol) and 1530 mL of formic acid were placed in a 3-L, 3-neck flask equipped with a mechanical stirrer, a temperature probe, a condenser, and a heating mantle. The reaction mixture was stirred overnight at 80 °C.The reaction mixture was allowed to cool and 770 mL of ethanol was added. The bright-green slurry was cooled to 0 ⁰C and stirred for two hours. The product was collected by filtration and washed with 700 mL of ethanol. The green-brown product was dried on the filter and then at 80 ⁰C under house vacuum to afford 300.1 g (75.2%) of the title compound.; Following in step e, ethyl 2-[(3-formylamino-4-methoxyphenyl)hydrazono]- propionate (6) and formic acid were placed in a reaction vessel and stirred overnight at 80 ⁰C. The reaction mixture was allowed to cool and ethanol was added. The bright-green slurry was cooled to 0 ⁰C and stirred. The product was collected by vacuum filtration, washed with ethanol, dried on a filter and dried at 80 ⁰C under vacuum to afford the desired indole, ethyl 6-fomiylamino-5-methoxy-lH-indole-2-carboxylate (7) via the Fischer Indole Synthesis.

References:

WO2006/102642,2006,A1 Location in patent:Page/Page column 9; 14; 1/6