Ammonium formate → HCID 63362875, compound

HRID 2178123Notes

Reaction equation

HRID 2178123 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>C(O)C>[CH3:19][O:18][C:11]1[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][C:5]1[N:6]=[N:7][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 63363216HCID 63363216, compound

Product 1

HCID 63362875HCID 63362875, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-chloro-N-(2,4-dimethoxybenzyl)pyridazin-3-amine (7.5 g, 26.9 mmol) in ethanol (250 mL) was added ammonium formate (5.94 g, 94.15 mmol) and the mixture was degassed with nitrogen three times. Palladium on charcoal (10 wt %, 2.14 g) was added and the mixture was degassed and recharged with nitrogen and stirred at 80° C. for 90 minutes under a nitrogen atmosphere. The mixture was filtered, concentrated to 15 mL and partitioned between DCM (200 mL) and water (150 mL). The organic layer was washed with brine (150 mL) and concentrated in vacuo. The residue was recrystallised from EtOAc to afford the title compound as cream coloured solid (4.5 g, 68%).

Workup

  1. customthe mixture was degassed with nitrogen three times
  2. additionPalladium on charcoal (10 wt %, 2.14 g) was added
  3. customthe mixture was degassed
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated to 15 mL
  6. custompartitioned between DCM (200 mL) and water (150 mL)
  7. washThe organic layer was washed with brine (150 mL)
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallised from EtOAc

Sources & evidence

ORD record
ord-4c079de8402746d8a2782f805b22c066
Source dataset
uspto-grants-2015_06
Patent number
US09067922B2

Reaction notes

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