Ammonium Hydroxide → 1-Chloro-4-hydrazinophthalazine

HRID 1042006Notes

Reaction equation

HRID 1042006 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](Cl)=[N:4][N:3]=1.[OH-].[NH4+:14].O.[NH2:16]N>C(O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:14][NH2:16])=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24654Hydrazine hydrate (1:1)2×HCID 784901,4-Dichlorophthalazine

Product 1

HCID 27937521-Chloro-4-hydrazinophthalazineYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1,4-dichlorophthalazine 23 (10.2 g, 51.2 mmol) and ammonium hydroxide (4.5 mL) in ethanol (110 mL) was heated to 60° C. Hydrazine hydrate (9 mL, 179 mmol) was added dropwise. After about one-half of the hydrazine hydrate was added, a thick precipitate formed. The mixture was stirred well and the temperature was kept below 74° C. by controlled addition of reagent. After the addition was complete the reaction was heated at reflux for 10 min, then allowed to cool. The reaction was filtered and the solids were washed with water (20 mL) and ethanol (20 mL), then dried at 40° C. in a vacuum oven overnight. The crude material was recrystallized from acetonitrile to afford 8.38 g (84%) of 11 as a yellow solid.

Workup

  1. customa thick precipitate formed
  2. additionthe temperature was kept below 74° C. by controlled addition of reagent
  3. additionAfter the addition
  4. temperaturewas heated
  5. temperatureat reflux for 10 min
  6. temperatureto cool
  7. filtrationThe reaction was filtered
  8. washthe solids were washed with water (20 mL) and ethanol (20 mL)
  9. customdried at 40° C. in a vacuum oven overnight
  10. customThe crude material was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-84d9e838625342caa8890767ce8c4dde
Source dataset
uspto-grants-2013_10
Patent number
US08557815B2

Reaction notes

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