Synthesis of Methoxatin

Structure of Methoxatin

C14H6N2O8

Principal investigator	Charles W. Rees
Publication year	1983
Synthesis type	Total
Number of steps	11 (linear)
References	J. Chem. Soc., Chem. Commun. 1983, 1372. Tetrahedron 1986, 42, 3259.

Part 1 of 1

intermediate structure

BnBr, K2CO3

Acetone

Reflux, 24 h, 92%

intermediate structure

LiAlH4

THF

0 °C, 2 h, 83%

intermediate structure

BaMnO4

CHCl3

Reflux, 60 min, 100%

intermediate structure

+

intermediate structure

NaOMe

MeOH, THF

-10 to 2 °C, 18 h, 90%

See the Aldol Condensation

intermediate structure

Xylene(s)

Reflux, 4 h, 82%

See the Hemetsberger-Knittel Indole Synthesis

intermediate structure

HCl

MeOH

Reflux, 6 h, 58%

intermediate structure

+

intermediate structure

HCl

CH2Cl2

RT, 24 h, 95%

See the Doebner-Miller Reaction

intermediate structure

Pd/C, H2

1 atm

MeOH

RT, 20 h, 89%

intermediate structure

Special reagent

CHCl3, MeOH

RT, 16 h, 93%

intermediate structure

TsOH, HC(OMe)3

MeOH

Reflux, 3 h

intermediate structure

HCl, K2CO3

H2O

85 °C, 4 h, 79% (2 steps)

intermediate structure

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