6-Chloro-3-hydrazinylpyridazine-4-carboxylic acid → 6-Chloro-8-carboxy-tetrazolo[1,5-b]pyridazine

HRID 1065846Notes

Reaction equation

HRID 1065846 reaction equation
[NH:1]([C:3]1[N:4]=[N:5][C:6]([Cl:12])=[CH:7][C:8]=1[C:9]([OH:11])=[O:10])[NH2:2].[N:13]([O-])=O.[Na+]>C(O)(=O)C.O>[Cl:12][C:6]1[CH:7]=[C:8]([C:9]([OH:11])=[O:10])[C:3]2[N:4]([N:13]=[N:2][N:1]=2)[N:5]=1

Participants

5

Reactant 2

HCID 205385786-Chloro-3-hydrazinylpyridazine-4-carboxylic acidHCID 23668193Sodium Nitrite

Product 1

HCID 205385646-Chloro-8-carboxy-tetrazolo[1,5-b]pyridazineYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To an ice-cold suspension of 3-hydrazino-4-carboxy-6-chloro-pyridazine (1.88 g; 0.01 mole) in 15% acetic acid, a solution of sodium nitrite (0.70 g) in water (5 ml) was added dropwise. After stirring for one hour at 5°-10° C. the separated precipitate was filtered, washed with anhydrous ethanol. The solid was suspended in 2 N HCl, the mixture was stirred for 30 minutes, the solid was stirred off, washed with cold water and dried under vacuum at 70° C. to give 1.73 g (87%) of the title compound, m.p. 225° C.

Workup

  1. filtrationwas filtered
  2. washwashed with anhydrous ethanol
  3. stirringthe mixture was stirred for 30 minutes
  4. stirringthe solid was stirred off
  5. washwashed with cold water
  6. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-6111e7bd95ba420eb7b22f5cb479adb9
Source dataset
uspto-grants-1982_05
Patent number
US04331666

Reaction notes

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