2-Hydrazinoethanol → 5-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbonitrile

HRID 1051643Notes

Reaction equation

C(O[CH:4]=[C:5]([C:8]#[N:9])[C:6]#[N:7])C.[NH:10]([CH2:12][CH2:13][OH:14])[NH2:11]>C(O)C>[NH2:9][C:8]1[N:10]([CH2:12][CH2:13][OH:14])[N:11]=[CH:4][C:5]=1[C:6]#[N:7]

Participants

Conditions

Temperature: 95 °C

Procedure

A 100-mL round-bottom flask was charged with 2-(ethoxymethylene)malononitrile (4.88 g, 39.96 mmol), ethanol (50 mL) and 2-hydrazinylethan-1-ol (4.4 g, 57.82 mmol). The resulting solution stirred for 10 h at 95° C. After cooling to room temperature, the reaction mixture was concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 9:1, dichloromethane/methanol) to afford 5-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbonitrile (3.9 g, 63%) as a yellow solid. MS (ESI, pos. ion) m/z 153 [M+H]+.

Workup

temperatureAfter cooling to room temperature
concentrationthe reaction mixture was concentrated under vacuum
customThe residue was purified via column chromatography on silica gel (eluting with 9:1, dichloromethane/methanol)

Sources & evidence

ORD record: ord-3fe485e15ca04b9c8e0fb656c6132dc8
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388161B2

Reaction notes

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