Reacción #1483050

Ecuación de reacción

HCl

sodium nitrite

ethyl 3-hydroxypropanimidate hydrochloride

acetamidine hydrochloride

hydrazine hydrate

→

2-(6-methyl-1,2,4,5-tetrazin-3-yl)ethanol

Rendimiento 49.9%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   ExtracciónThe aqueous solution was extracted with methylene chloride (5×50 mL)
3. 3
   Secadodried with magnesium sulfate
4. 4
   Otrothe solvent was removed by rotary evaporation
5. 5
   Otrodried under vacuum

Procedimiento

To a mixture of ethyl 3-hydroxypropanimidate hydrochloride (2 mmol, 307 mg) and acetamidine hydrochloride (10 mmol, 945 mg) was added hydrazine hydrate (2 mL) under an atmosphere of argon. After stirring at room temperature for 2 hours, the mixture was diluted with water (25 mL) and sodium nitrite (25 mmol, 1.72 g) was added. To this solution was added 2% aqueous HCl dropwise on an ice bath until the now pink solution reached a pH of 3. The aqueous solution was extracted with methylene chloride (5×50 mL), dried with magnesium sulfate, the solvent was removed by rotary evaporation, and then dried under vacuum to afford the product, 2-(6-methyl-1,2,4,5-tetrazin-3-yl)ethanol (140 mg, 37%), as a pink oil. LRMS-ESI [M+H]+ calcd. for C5H9N4O+: 141.08, found: 140.7.

Fuente