Stannous Chloride → 3-hydrazino-N-methoxy-4-methyl-benzamide

Temperatur

0 °C

To a stirred solution of 3-amino-N-methoxy-4-methyl-benzamide 1 (102 mg, 0.56 mmol, preparation: International Patent Application Publication No. WO 02/40486 A2, pg. 66) in water (5 ml) at 0° C. was added conc. HCl (5 mL) followed by the addition of sodium nitrite (43 mg, 0.62 mmol). The reaction mixture was stirred at 0° C. for 40 min then a solution of tin(II)chloride (241 mg, 1.27 mmol) in conc. HCl (1 mL) was added and the mixture was stirred for 1 hr then allowed to stand at −20° C. for 20 hr before it was warmed to RT and concentrated to a white solid. The solid was triturated with ethanol, the solids were filtered, and the filtrate concentrated to provide 3-hydrazino-N-methoxy-4-methyl-benzamide 2 as white solid (486 mg) as a mixture with tin salts and ethanol which was used without further purification. HPLC (6 minute gradient) tR 0.78 min; MS m/z 195.9 [M+H]+.

1. stirringthe mixture was stirred for 1 hr
2. waitto stand at −20° C. for 20 hr before it
3. temperaturewas warmed to RT
4. concentrationconcentrated to a white solid
5. customThe solid was triturated with ethanol
6. filtrationthe solids were filtered
7. concentrationthe filtrate concentrated

ORD-Eintrag

ord-09d3d41fb1eb41f2bf93f11374cd06be

Quelldatensatz

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08242117B2