Ammonium Hydroxide → 3-Amino-4-methyl-6-phenylpyridazine

HRID 1731714Notes

Reaction equation

HRID 1731714 reaction equation
F[C:2]1[N:3]=[N:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:7]=1[CH3:8].[NH4+:15].[OH-]>>[NH2:15][C:2]1[N:3]=[N:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:7]=1[CH3:8]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 20226921HCID 20226921, compound

Product 1

HCID 6039463-Amino-4-methyl-6-phenylpyridazine

Procedure

A mixture of 3-fluoro-4-methyl-6-phenylpyridazine (1.0 g) and 50 mL of 28% aqueous NH4OH is heated in a pressure bottle to 95°-100° C. The reaction mixture is cooled and thereafter extracted with CH2Cl2. The organic materials are then extracted with 10% aqueous HCl. The acid phase is washed with CH2Cl2, cooled and basified with caustic. The resulting mixture is extracted several times with CH2Cl2. The organic extracts are then combined and dried with MgSO4 and the remaining liquid is concentrated to give 550 mg (56%) crude product as a yellow solid. Recrystallization from EtOH gives an analytically pure material melting at 132°-134° C.

Workup

  1. temperatureis heated in a pressure bottle to 95°-100° C
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with CH2Cl2
  4. extractionThe organic materials are then extracted with 10% aqueous HCl
  5. washThe acid phase is washed with CH2Cl2
  6. temperaturecooled
  7. extractionThe resulting mixture is extracted several times with CH2Cl2
  8. dry with materialdried with MgSO4
  9. concentrationthe remaining liquid is concentrated
  10. customto give 550 mg (56%) crude product as a yellow solid
  11. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-024c20ff669c403880afa27339861173
Source dataset
uspto-grants-1986_11
Patent number
US04623376

Reaction notes

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