Hydrazine hydrate (1:1) → 8-Amino-5-(imidazol-1-yl)-7-phenylpyrido[3,4-d]pyridazine-l,4(2H,3H)dione

HRID 37499Notes

Reaction equation

HRID 37499 reaction equation
[NH2:1][C:2]1[C:3]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:4][C:5]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[C:6]([C:13](OCC)=[O:14])[C:7]=1[C:8](OCC)=[O:9].O.[NH2:30][NH2:31]>C(O)C>[NH2:1][C:2]1[C:7]2[C:8](=[O:9])[NH:31][NH:30][C:13](=[O:14])[C:6]=2[C:5]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[N:4][C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 152897003-Amino-4,5-diethoxycarbonyl-6-(imidazol-1-yl)-2-phenylpyridine

Product 1

HCID 152896798-Amino-5-(imidazol-1-yl)-7-phenylpyrido[3,4-d]pyridazine-l,4(2H,3H)dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 10ml of ethanol was dissolved 0.342 g of 3-amino-4,5-diethoxycarbonyl-6-(imidazol-1-yl)-2-phenylpyridine, and 0.5 ml of hydrazine monohydrate was added to the solution. The mixture was heated under reflux for 7 hours. After the reaction mixture was concentrated, the residue was acidified with acetic acid. The resulting precipitate was collected with. filtration and washed with water, followed by reprecipitation from DMF/H2O, to give 0.2 g of the title compound as yellow powder.

Workup

  1. additionwas added to the solution
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 7 hours
  4. concentrationAfter the reaction mixture was concentrated
  5. customThe resulting precipitate was collected with
  6. filtrationfiltration
  7. washwashed with water
  8. customfollowed by reprecipitation from DMF/H2O

Sources & evidence

ORD record
ord-95fc3b27fc0944679c33786bb2fb1fea
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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