Triethylamine → Ethyl 5-[amino(hydroxyimino)methyl]pyrazine-2-carboxylate

HRID 2242223Notes

Reaction equation

C(N(CC)CC)C.[CH2:8]([O:10][C:11]([C:13]1[CH:18]=[N:17][C:16]([C:19]#[N:20])=[CH:15][N:14]=1)=[O:12])[CH3:9].Cl.[NH2:22][OH:23]>CCO>[NH2:20][C:19](=[N:22][OH:23])[C:16]1[N:17]=[CH:18][C:13]([C:11]([O:10][CH2:8][CH3:9])=[O:12])=[N:14][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Triethylamine (7.08 mL, 51.9 mmol) was added to a solution of 5-cyano-pyrazine-2-carboxylic acid ethyl ester (4.0 g, 22.6 mmol), hydroxylamine hydrochloride (3.45 g, 49.7 mmol) and EtOH (32 mL) and stirred at 80° C. for 12 hours. The reaction mixture was cooled to room temperature, concentrated in vacuo and dissolved in H2O (30 mL). The aqueous solution was extracted with CHCl3 (3×30 mL) and the combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to yield the title compound (2.95 g, 62%) as a yellow solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
dissolutiondissolved in H2O (30 mL)
extractionThe aqueous solution was extracted with CHCl3 (3×30 mL)
dry with materialthe combined organic extracts were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-61fa46744f05455282fc975e651a52b8
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671043B2

Reaction notes

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