Hydrazine hydrate (1:1) → 6-Chloro-3-hydrazinylpyridazine-4-carboxylic acid

HRID 1065845Notes

Reaction equation

HRID 1065845 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:11])=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].O.[NH2:13][NH2:14]>C(O)C>[NH:13]([C:2]1[N:3]=[N:4][C:5]([Cl:11])=[CH:6][C:7]=1[C:8]([OH:10])=[O:9])[NH2:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 4338043,6-Dichloropyridazine-4-carboxylic acid

Product 1

HCID 205385786-Chloro-3-hydrazinylpyridazine-4-carboxylic acidYield 93.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 3,6-dichloro-4-carboxy-pyridazine (20 g; 0.103 mole) and 22 ml of 98% hydrazine hydrate in 200 ml of 50% ethanol was refluxed, under stirring, for one hour. After cooling at 5° C., the solid precipitate was collected, washed with 20 ml of anhydrous ethanol. The solid was suspended in 100 ml of water, the mixture was brought to pH 1-2 with 23% HCl, after cooling at 5° C. the solid was filtered, dried under vacuum at 80° C. to give 18.29 g (93.4%) of the title compound, m.p. 198°-201° C.

Workup

  1. temperaturewas refluxed
  2. customthe solid precipitate was collected
  3. washwashed with 20 ml of anhydrous ethanol
  4. temperatureafter cooling at 5° C. the solid
  5. filtrationwas filtered
  6. customdried under vacuum at 80° C.

Sources & evidence

ORD record
ord-c9243d78b3eb41bdbf134efdfe3bf42c
Source dataset
uspto-grants-1982_05
Patent number
US04331666

Reaction notes

Loading…