Hydrazine → 1H-Imidazo[4,5-d]pyridazine-4,7-diol

HRID 42228

Reaction equation

HRID 42228 reaction equation
CO[C:3]([C:5]1[N:6]=[CH:7][NH:8][C:9]=1[C:10]([O:12]C)=O)=[O:4].[NH2:14][NH2:15]>CO>[NH:6]1[C:5]2[C:3](=[O:4])[NH:14][NH:15][C:10](=[O:12])[C:9]=2[N:8]=[CH:7]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 768101H-Imidazole-4,5-dicarboxylic acid, 4,5-dimethyl ester

Product 1

HCID 2229231H-Imidazo[4,5-d]pyridazine-4,7-diolYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
115 °C

Procedure

1H-Imidazole-4,5-dicarboxylic acid dimethyl ester (592 mg, 3.21 mmol) is combined with hydrazine (600 mg, 18.8 mmol) and MeOH (10 mL). The reaction mixture is heated to 115° C. for 30 min. Cool and filter off the resulting precipitate. Wash with additional water. Combine the precipitate with hydrazine (1.38 mL) and reflux for 4 h. Pour the reaction mixture into ice water and adjust the to pH 2 with HCl (12 N). The new precipitate is isolated by filtration to afford the title product (293 mg, 60%)

Workup

  1. temperatureCool
  2. filtrationfilter off the resulting precipitate
  3. washWash with additional water
  4. temperaturereflux for 4 h
  5. additionPour the reaction mixture into ice water
  6. customThe new precipitate is isolated by filtration

Sources & evidence

ORD record
ord-6c20aee492c64863989a5efab42e3ca4
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Linked notes

Loading…