Hydrazine hydrate (1:1) → 6-Hydrazinonicotinic acid

HRID 1290606Notes

Reaction equation

HRID 1290606 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.O.[NH2:12][NH2:13]>O.Cl>[NH:12]([C:2]1[N:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:9][CH:10]=1)[NH2:13]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 792226-Chloronicotinic acid

Product 1

HCID 37826176-Hydrazinonicotinic acidYield 77%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

6-Chloronicotinic acid (8.0 g) was added to 85% hydrazine hydrate (35 ml). The reaction mixture was placed in a 100° C oil bath for 4 hours. The homogeneous reaction mixture was concentrated to dryness to give a white solid. The solid was dissolved in water and on acidification to pH 5.5 with concentrated hydrochloric acid a precipitate formed. The precipitate was isolated by filtration and the solid was washed with 95% ethanol and ether to give 6.0 g of a pale brown solid; yield 77% m.p. 292°-293° C.;

Workup

  1. customwas placed in a 100° C
  2. customfor 4 hours
  3. concentrationThe homogeneous reaction mixture was concentrated to dryness
  4. customto give a white solid
  5. customformed
  6. customThe precipitate was isolated by filtration
  7. washthe solid was washed with 95% ethanol and ether

Sources & evidence

ORD record
ord-3f6b1c88c9104db0a89038a6d46c756c
Source dataset
uspto-grants-1998_05
Patent number
US05753520

Reaction notes

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