Hydrochloric Acid → Pyridazin-3-ylmethanamine hydrochloride

HRID 2203346Notes

Reaction equation

HRID 2203346 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[N:8])[N:2]=1.[ClH:9].[H][H]>CO.[Pd]>[ClH:9].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[N:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13642940Pyridazine-3-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 53419881Pyridazin-3-ylmethanamine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the intermediate from Step B (5.96 g, 56.7 mmol) in MeOH (35 mL) was added 6N HCl (20.89 mL, 125 mmol) followed by Pd/C (0.905 g, 8.51 mmol). The reaction mixture was kept on Parr shaker for 2 hours at 40 psig hydrogen. The reaction mixture was filtered through Celite™ (diatomaceous earth) and washed with 600 mL of MeOH and the filtrate concentrated. The residue was azeotroped several times with toluene. A dark brown solid was obtained. m/z=110 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite™ (diatomaceous earth)
  2. washwashed with 600 mL of MeOH
  3. concentrationthe filtrate concentrated
  4. customThe residue was azeotroped several times with toluene
  5. customA dark brown solid was obtained

Sources & evidence

ORD record
ord-9702980e4c77474cb8078c16557fa62e
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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