Azane;hydrate → 6-Isopropylpyridazin-3-amine

HRID 1946450Notes

Reaction equation

HRID 1946450 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:6][CH:7]=1.O.[NH3:12]>O>[NH2:12][C:2]1[N:3]=[N:4][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12896473Azane;hydrateHCID 178045553-Chloro-6-(propan-2-yl)pyridazine

Product 1

HCID 230281096-Isopropylpyridazin-3-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

3-Chloro-6-isopropylpyridazine (1.60 g, 10.2 mmol) and 28% ammonia water (15.0 ml) were introduced into a sealed tube reactor and stirred under pressure and heating at 140° C. for 24 hours and at 165° C. for 25 hours. The reaction solution was left and cooled, poured into water (30.0 ml), adjusted to pH 9, and extracted 3 times with ethyl acetate. The extracts were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude crystals. The crystals, while being washed with diisopropyl ether-hexane, were filtered to give the title compound as pale brown crystals. The yield was 0.41 g (29.3%).

Workup

  1. waitThe reaction solution was left
  2. temperaturecooled
  3. extractionextracted 3 times with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give crude crystals
  7. washThe crystals, while being washed with diisopropyl ether-hexane
  8. filtrationwere filtered

Sources & evidence

ORD record
ord-76327389dcab4f66b5dd52832d895c8c
Source dataset
uspto-grants-2013_03
Patent number
US08399381B2

Reaction notes

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