Hydrazine hydrate (1:1) → 3-Aminopyrazine-2-carbohydrazide

HRID 1749666Notes

Reaction equation

HRID 1749666 reaction equation
O.[NH2:2][NH2:3].[NH2:4][C:5]1[C:6]([C:11]([O:13]C)=O)=[N:7][CH:8]=[CH:9][N:10]=1>C(O)C>[NH2:4][C:5]1[C:6]([C:11]([NH:2][NH2:3])=[O:13])=[N:7][CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 72669Methyl 3-aminopyrazinecarboxylate

Product 1

HCID 12401093-Aminopyrazine-2-carbohydrazideYield 97.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Hydrazine monohydrate (34 mL, 1094.95 mmol) was added portionwise to a stirred suspension of methyl 3-aminopyrazine-2-carboxylate (21.3 g, 139.09 mmol) in ethanol (65 mL) at r.t. The resulting slurry was stirred at 60° C. for 2 hours, cooled to room temperature and filtered. The solid was washed with cold ethanol (2×25 ml) and dried to a constant weight to afford 3-aminopyrazine-2-carbohydrazide (20.75 g, 97%) as a beige solid: 1H NMR Spectrum; (DMSO-d6) 4.49 (2H, d), 7.46 (2H, br s), 7.78 (1H, d), 8.17 (1H, d), 9.79 (1H, t); Mass Spectrum [M+H]+=154.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe solid was washed with cold ethanol (2×25 ml)
  4. customdried to a constant weight

Sources & evidence

ORD record
ord-9e51f439ccd44c1e98aeb491cd3f1d00
Source dataset
uspto-grants-2015_10
Patent number
US09156831B2

Reaction notes

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