Water → 3-Amino-6-bromopyrazine-2-carbohydrazide

HRID 2204856Notes

Reaction equation

HRID 2204856 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].O>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

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylate

Product 1

HCID 580702563-Amino-6-bromopyrazine-2-carbohydrazideYield 96.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 3-amino-6-bromo-pyrazine-2-carboxylate (10.18 g, 43.87 mmol) was suspended in EtOH (50.90 mL) and hydrazine hydrate (4.392 g, 4.268 mL, 87.74 mmol) was added and the reaction mixture heated at 70° C. for 2 h. Water (50 mL) was added and the precipitate isolated by filtration. The solid was washed with methanol and dried under vacuum to leave the product as a pale yellow powder (9.8 g, 96% yield); 1H NMR (400 MHz, DMSO) d 4.53 (bs s, 2H), 7.62 (br s, 2H) and 9.78 (br s, 1H) ppm; MS (ES+) 232.06

Workup

  1. customthe precipitate isolated by filtration
  2. washThe solid was washed with methanol
  3. customdried under vacuum

Sources & evidence

ORD record
ord-4182e074fd96418a852fc6d5ececfe32
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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