Hydrazine hydrate (1:1) → 4-(tert-Butyl)-3-chloro-6-hydrazinylpyridazine

HRID 378839

Reaction equation

HRID 378839 reaction equation
[C:1]([C:5]1[CH:10]=[C:9](Cl)[N:8]=[N:7][C:6]=1[Cl:12])([CH3:4])([CH3:3])[CH3:2].O.[NH2:14][NH2:15]>C(O)C>[C:1]([C:5]1[CH:10]=[C:9]([NH:14][NH2:15])[N:8]=[N:7][C:6]=1[Cl:12])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 898464-tert-Butyl-3,6-dichloropyridazine

Product 1

HCID 229878864-(tert-Butyl)-3-chloro-6-hydrazinylpyridazineYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-t-Butyl-3,6-dichloropyridazine (Samaritoni, J. G.; Org. Prep. & Proc. Intl., 1988, 20(2), 117-121) (16 g, 78 mmol) and hydrazine monohydrate (24.7 mL, 780 mmol) in ethanol (250 mL) were heated at reflux for 16 hours. The solvent was removed and hydrochloric acid (5M) was added and the resulting mixture was washed with dichloromethane. The aqueous layer was poured onto ice and ammonium hydroxide was added until the mixture was basic. The mixture was extracted with dichoromethane, dried (MgSO4) filtered and evaporated to give a yellow solid (9.5 g, 61%) 1HNMR (360 MHz, CDCl3) δ 1.46 (9H, s, t Bu), 378 (2H, br s, NH2), 6.84 (1H, br s, NH), 7.10 (1H, s, ArH); MS (ES+) m/e 201 [MH+].

Workup

  1. temperatureat reflux for 16 hours
  2. customThe solvent was removed
  3. additionhydrochloric acid (5M) was added
  4. washthe resulting mixture was washed with dichloromethane
  5. additionThe aqueous layer was poured onto ice and ammonium hydroxide
  6. additionwas added until the mixture
  7. extractionThe mixture was extracted with dichoromethane
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-66c584cfab254be3bca3e97024ab1cf7
Source dataset
uspto-grants-2001_10
Patent number
US06297235B1

Linked notes

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