tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate Chemical Properties

Melting point:

74-77 °C

Density 

1.117±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

10.38±0.43(Predicted)

form 

Solid

color 

White to Pale Yellow

CAS DataBase Reference

198904-85-7(CAS DataBase Reference)

tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate Usage And Synthesis

Chemical Properties

White Solid

Uses

An intermediate for the preparation of antiviral protease inhibitors.

Synthesis

Step 1: A mixture of 4-(pyridin-2-yl)benzaldehyde X (17.7 g, 96.6 mmol) and tert-butylcarbamate (12.2 g, 92.3 mmol) in ethanol (125 mL) was kept at reflux under nitrogen for 4 hours (h). The reaction mixture was cooled to 40 ??C and ice (60 g) was added. The resulting mixture was stirred for 20 minutes (min). The precipitate was collected by filtration, washed with water and dried in a vacuum oven (60 ??C). Product XII, yield 25.0 g, 91%.

Step 2: A solution of the above product (23.15 g, 77.85 mmol) in methanol (350 ml) was treated with 20% palladium activated charcoal (2.3 g, 50% wet) and hydrogenated at 10 psi for 4 hours. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed with methanol and the solvent was removed in a rotary evaporator. The residue was recrystallized with heptane and dried in a vacuum oven (40 ??C). The product 2-[4-(2-pyridinyl)benzyl]-hydrazinecarboxylic acid tert-butyl ester was obtained in a yield of 2.48 g, 97%.

tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate(198904-85-7)Related Product Information

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