Phthalazine → 1,2-Phenylenedimethanamine

HRID 711599Notes

Reaction equation

HRID 711599 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[N:3][N:2]=1.[H][H]>[Pd].[Ni].CO>[C:5]1([CH2:4][NH2:3])[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[CH2:1][NH2:2]

Participants

6

Reactant 2

HCID 9207PhthalazineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 4319681,2-Phenylenedimethanamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Phthalazine (21.5 g, 0.165 mol), 10% palladium on carbon (2 g), and methanol (125 mL) were combined in a pressure bottle and shaken at room temperature under 60 psi of hydrogen for 5 days. Raney-nickel® slurry (6.42 g) and 10% palladium on carbon (0.50 g) were added, and the mixture was shaken at 50° C. under 60 psi of hydrogen for 16 hours. The mixture was filtered through a nylon membrane and concentrated to give the titled compound: 1H NMR (300 MHz, DMSO-d6) δ ppm 7.32 (dd, J=5.4, 3.5 Hz, 2H), 7.17 (dd, J=5.6, 3.4 Hz, 2H), 3.74 (s, 4H); MS (DCI/NH3) m/z 137 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8a1f22d1dcda48139649534856a44378
Source dataset
uspto-grants-2015_11
Patent number
US09181275B2

Reaction notes

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