Hydrochloric Acid → HCID 58490215, compound

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.

1. additionwas added
2. extractionThe aqueous solution was extracted with methylene chloride (5×25 mL)
3. dry with materialdried with magnesium sulfate
4. customthe solvent was removed by rotary evaporation
5. customdried under vacuum

ORD record

ord-329fffbaab16486a82f6b8e7f678260c

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08900549B2