Hydrazine → Pyrazine-2-Carboxylic Acid Hydrazide

HRID 1368167Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([O:9]C)=O.[NH2:11][NH2:12]>>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([NH:11][NH2:12])=[O:9]

Participants

Reactant 2

HCID 9321Hydrazine

HCID 72662Methyl pyrazinoate

Product 1

HCID 258796Pyrazine-2-Carboxylic Acid Hydrazide

Procedure

A solution of methyl pyrazinecarboxylate (600 mg, 4.34 mmol) in hydrazine (3 ml) was stirred overnight for 20 hours, then at 60° C. for 4 hours. Removal of excess hydrazine under high vacuum afforded pyrazine hydrazide intermediate 47 as a yellow solid (550 mg, 92%). 1H NMR: (CD3OD) δ 9.19 (d, J=1.5, 1H), 8.76 (d, J=2.4, 1H), 8.65 (app t, 1H); LC/MS: (ES+) m/z (M+H)+=139, HPLC Rt=0.087.

Workup

customRemoval of excess hydrazine under high vacuum

Sources & evidence

ORD record: ord-d27fb790976646aebab8d8741918a30d
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573262B2

Reaction notes

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