Hydrazine hydrate (1:1) → 3-Amino-6-bromopyrazine-2-carbohydrazide

HRID 1959419Notes

Reaction equation

HRID 1959419 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]=1

Participants

4

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

  1. customforming a thick yellow solid
  2. customThe solid was isolated by filtration
  3. washwashed with water (20 mL) and ethanol (40 mL)
  4. 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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