Synthesis of Methoxatin

Structure of Methoxatin

C14H6N2O8

Principal investigator	Elias J. Corey
Publication year	1981
Synthesis type	Total
Number of steps	9 (linear)
References	J. Am. Chem. Soc. 1981, 103, 5599.

Part 1 of 1

intermediate structure

HCO2Ac

HCO2H

RT to 50 °C, 30 min, 95%

intermediate structure

PtO2, H2

3 atm

EtOH

65 °C, 93%

intermediate structure

+

intermediate structure

NaNO2, HCl

H2O, MeOH

0 °C, 8 h, 80%

See the Japp-Klingemann Reaction

intermediate structure

HCO2H

80 °C, 10 h, 72%

See the Fischer Indole Synthesis

intermediate structure

HCl

Acetone, H2O

Reflux, 60 min, 79%

intermediate structure

+

intermediate structure

HCl

CH2Cl2

RT, 17 h, 90%

See the Doebner-Miller Reaction

intermediate structure

(NH4)2Ce(NO3)6

H2O, MeCN

0 °C, 10 min, 60%

intermediate structure

TsOH

HC(OMe)3

Reflux, 4 h, 92%

intermediate structure

HCl, K2CO3

H2O

85 °C, 4 h, 98%

intermediate structure

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