Hydrazinecarboxylic acid, ethyl ester → 3-(6-chloro-4-methylpyridin-2-yl)-1H-1,2,4-triazol-5 (4H)-one

HRID 1476913Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([CH3:10])[CH:3]=1.[NH:11]([C:13]([O:15]CC)=O)[NH2:12]>CN1C(=O)CCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:13](=[O:15])[NH:11][N:12]=2)[CH:5]=[C:4]([CH3:10])[CH:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 6-chloro-4-methylpicolinonitrile (3 g, 19.66 mmol) and ethyl hydrazinecarboxylate (8.19 g, 79 mmol) in NMP (6 mL) was heated in a sealed tube at 160° C. overnight. The residue was purified by column chromatography eluting with a gradient of 0-80% EtOAc in heptanes. The product-containing fractions were collected and evaporated in vacuo to give the title compound as a yellow semi-solid (428 mg). ESI-MS m/z [M+H]+211.6.

Workup

customThe residue was purified by column chromatography
washeluting with a gradient of 0-80% EtOAc in heptanes
customThe product-containing fractions were collected
customevaporated in vacuo

Sources & evidence

ORD record: ord-ce9153a9fa4549f4849fb0861e1c08c5
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09402841B2

Reaction notes

Loading…