Hydrazine hydrate (1:1) → 3-Amino-6-bromopyrazine-2-carbohydrazide
Reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.O.[NH2:14][NH2:15]>CCO>[NH2:1][C:2]1[C:3]([C:9]([NH:14][NH2:15])=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a suspension of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (2.5 g, 10.8 mmol) in EtOH (50 mL) was added hydrazine hydrate (3.2 g, 3.1 mL, 64.6 mmol) and the reaction mixture was heated at 70° C. for 1.5 h forming a thick yellow solid. The solid was isolated by filtration, washed with water (20 mL) and ethanol (40 mL). The solid was dried under high vacuum to yield 3-amino-6-bromo-pyrazine-2-carbohydrazide (2.35 g, 94%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.78 (s, 1H), 8.31 (s, 1H), 7.62 (s, 2H), 4.53 (d, =3.5 Hz, 2H). LC/MS m/z 233.1 [M+H]+.
Workup
- customforming a thick yellow solid
- customThe solid was isolated by filtration
- washwashed with water (20 mL) and ethanol (40 mL)
- customThe solid was dried under high vacuum
Sources & evidence
- ORD record
- ord-c7c5bc9710e146c785144800cdc36850
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410112B2
Reaction notes
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