Reaction #1483051

Reaction equation

HCl

sodium nitrite

ethyl 3-hydroxypropanimidate hydrochloride

formamidine acetate

hydrazine hydrate

→

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

Yield 22.2%

Solvents

water

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   ExtractionThe aqueous solution was extracted with methylene chloride (5×25 mL)
3. 3
   Dryingdried with magnesium sulfate
4. 4
   Otherthe solvent was removed by rotary evaporation
5. 5
   Otherdried under vacuum

Procedure

To a mixture of ethyl 3-hydroxypropanimidate hydrochloride (1 mmol, 153 mg) and formamidine acetate (5 mmol, 521 mg) was added hydrazine hydrate (1 mL) under an atmosphere of argon. After stirring at room temperature for 2 hours, the mixture was diluted with water (10 mL) and sodium nitrite (12.5 mmol, 0.86 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 (5×25 mL), dried with magnesium sulfate, the solvent was removed by rotary evaporation, and then dried under vacuum to afford the product, 2-(1,2,4,5-tetrazin-3-yl)ethanol (28 mg, 22%), as a pink oil. LRMS-ESI [M+H]+ calcd. for C4H7N4O+: 127.06, found: 126.7.

Source