Acetic Acid → 1-(3,4-Dimethoxy-phenyl)-4-hydroxy-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid amide

HRID 1818698Notes

Reaction equation

HRID 1818698 reaction equation
C[O:2][C:3]([C:5]1[C:10]([OH:11])=[CH:9][C:8](=[O:12])[N:7]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[N:6]=1)=O.C(O)(=O)C.[NH3:27]>CO>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([N:7]2[C:8](=[O:12])[CH:9]=[C:10]([OH:11])[C:5]([C:3]([NH2:27])=[O:2])=[N:6]2)[CH:18]=[CH:17][C:16]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 222AmmoniaHCID 578861981-(3,4-Dimethoxy-phenyl)-4-hydroxy-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid methyl ester

Product 1

HCID 578862251-(3,4-Dimethoxy-phenyl)-4-hydroxy-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The pyridazine (29) (295 mg) was dissolved in 3 ml of 7N NH3 in methanol and heated to reflux in a sealed tube for 4 hours. The reaction was allowed to cool, neutralized with acetic acid, and concentrated to dryness to give 266 mg of desired amide (30) as a solid. MS+: m/e=292.0 (M+H).

Workup

  1. temperatureheated
  2. temperatureto reflux in a sealed tube for 4 hours
  3. temperatureto cool
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-722d677b3d0448b4a4567053d11ce2bf
Source dataset
uspto-grants-2009_10
Patent number
US07601718B2

Reaction notes

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