Potassium Hydroxide → 6-Hydrazinonicotinic acid

HRID 242234Notes

Reaction equation

HRID 242234 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].[OH-].[K+]>C(O)C>[NH:12]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1)[NH2:13]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 792226-Chloronicotinic acid

Product 1

HCID 37826176-Hydrazinonicotinic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

5.0 g (31.7 mmol) 6-chloronicotinic acid and 30.9 ml (31.8 g, 634.7 mmol) hydrazine hydrate are initially introduced into 10 ml ethanol and the mixture is stirred at the boiling point at a bath temperature of 100° C. for 16 h. The solvent and excess hydrazine hydrate are distilled off on a rotary evaporator, the residue is taken up in water, 1.8 g (31.7 mmol) potassium hydroxide are then added and the mixture is stirred for 15 min. The solvent is removed completely on a rotary evaporator, the residue is dried in vacuo and 7.5 g of crude product, which is reacted further as such, are obtained.

Workup

  1. distillationThe solvent and excess hydrazine hydrate are distilled off on a rotary evaporator
  2. stirringthe mixture is stirred for 15 min
  3. customThe solvent is removed completely on a rotary evaporator
  4. dry with materialthe residue is dried in vacuo and 7.5 g of crude product, which
  5. customis reacted further as such,
  6. customare obtained

Sources & evidence

ORD record
ord-6259cf52582b48108f4ebac381dddc85
Source dataset
uspto-grants-2014_02
Patent number
US08653111B2

Reaction notes

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