Methanol → 3-Amino-6-(3-pyridyl)pyrazine-2-carbohydrazide

HRID 78605Notes

Reaction equation

HRID 78605 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([O:16]C)=O)=[N:4][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][N:7]=1.[NH2:18][NH2:19].CO>O>[NH2:1][C:2]1[C:3]([C:14]([NH:18][NH2:19])=[O:16])=[N:4][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 59471788Methyl 3-amino-6-(3-pyridyl)pyrazine-2-carboxylate

Product 1

HCID 594724013-Amino-6-(3-pyridyl)pyrazine-2-carbohydrazideYield 58.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 3-amino-6-(3-pyridyl)pyrazine-2-carboxylate (2 g, 8.687 mmol) was heated in hydrazine (1.392 g, 1.363 mL, 43.43 mmol) with a minimal amount of MeOH (5 mL) added at 80° C. for 2 hours. The reaction was treated with water and the product collected by filtration, washed with methanol and dried to give the desired product as a brown solid (1.17 g, 58% Yield). 1H NMR (400.0 MHz, DMSO) d 7.43 (1H, m), 7.47 (2H, br s), 8.54 (2H, m), 8.90 (1H, s), 9.38 (1H, m), 10.16 (1H, br s); MS (ES+) 231.96

Workup

  1. additionadded at 80° C. for 2 hours
  2. filtrationthe product collected by filtration
  3. washwashed with methanol
  4. customdried

Sources & evidence

ORD record
ord-402fca6998994a0ba1f59af19925220c
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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