Hydrazine hydrate (1:1) → 4-bromo-N-(5-(hydrazinecarbonyl)thiophen-3-yl)picolinamide

HRID 2091611Notes

Reaction equation

HRID 2091611 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:12]=[C:13]([C:16]([O:18]C)=O)[S:14][CH:15]=2)=[O:9])[CH:3]=1.O.[NH2:21][NH2:22]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:12]=[C:13]([C:16]([NH:21][NH2:22])=[O:18])[S:14][CH:15]=2)=[O:9])[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66628543Methyl 4-(4-bromopicolinamido)thiophene-2-carboxylate

Product 1

HCID 666284524-bromo-N-(5-(hydrazinecarbonyl)thiophen-3-yl)picolinamideYield 101.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The methyl 4-(4-bromopicolinamido)thiophene-2-carboxylate (2.7 g, 6.9 mmol) was dissolved in ethanol, hydrazine hydrate (1.4 mL, 28 mmol) was added and the reaction was refluxed overnight. The reaction mixture was concentrated, and the solids were suspended in acetonitrile and filtered to afford 2.4 g (70%) 4-bromo-N-(5-(hydrazinecarbonyl)thiophen-3-yl)picolinamide as a white solid. M+1=341.1

Workup

  1. temperaturethe reaction was refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-8e3c567faaa84e1ebc8cbb177885228e
Source dataset
uspto-grants-2013_05
Patent number
US08440665B2

Reaction notes

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