Hydrazine hydrate (1:1) → 2-Hydrazinylpyridine-4-carboxylic acid

HRID 514322Notes

Reaction equation

HRID 514322 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][N:3]=1.O.[NH2:12][NH2:13]>O1CCOCC1>[NH:12]([C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][N:3]=1)[NH2:13]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2369852-Chloroisonicotinic acid

Product 1

HCID 269672462-Hydrazinylpyridine-4-carboxylic acidYield 42%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-chloropyridine-4-carboxylic acid (1.57 g, 100 mmol) in 1,4-dioxane (30 mL) was added hydrazine hydrate (1.0 g, 200 mmol) dropwise at rt. The reaction mixture was heated at 100° C. overnight. The mixture was concentrated, and the residue was purified by flash column chromatography (CH2Cl2/MeOH=20/1) to afford the title compound (650 mg, 42%) as a white solid. [M+H] Calc'd for C6H7N3O2, 154. Found, 154.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash column chromatography (CH2Cl2/MeOH=20/1)

Sources & evidence

ORD record
ord-228083a46d1342b58fd2c48a39f9ac3f
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

Loading…