Hydrazine → 5-Chloropyridine-3-carbohydrazide

HRID 1777032Notes

Reaction equation

HRID 1777032 reaction equation
[NH2:1][NH2:2].[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:13]=1)[C:9](OC)=[O:10]>CO>[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:13]=1)[C:9]([NH:1][NH2:2])=[O:10]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 15421663Methyl 5-chloropyridine-3-carboxylate

Product 1

HCID 144441945-Chloropyridine-3-carbohydrazideYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Hydrazine (17.93 mg, 0.560 mmol) was added to methyl 5-chloronicotinate (80 mg, 0.466 mmol) in methanol (8 mL) and heated overnight at 70° C. The reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and the compound was purified by column chromatography affording the title compound (40 mg). 1H NMR (400 MHz, CD3OD): δ 8.85 (d, 1H, J=2.0 Hz), 8.70 (d, 1H, J=2.4 Hz), 8.22 (t, 1H, J=2.0 Hz). ESI-MS: 172.0 [M+H]+.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by vacuum
  3. customthe compound was purified by column chromatography

Sources & evidence

ORD record
ord-ab36e221f5514819896104a48ef4c6e0
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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