HCID 13730343, compound → HCID 13730344, compound

HRID 652712Notes

Reaction equation

HRID 652712 reaction equation
[ClH:1].[C:2]1([CH2:14][NH2:15])[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH:7]=[CH:6][CH:5]=[C:4]3[CH:3]=1.[H][H]>CO.[Pd]>[ClH:1].[CH:2]1([CH2:14][NH2:15])[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH:7]=[CH:6][CH:5]=[C:4]3[CH2:3]1

Participants

5

Reactant 2

HCID 13730343HCID 13730343, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 13730344HCID 13730344, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The N-[(1-acenaphthylenyl)methyl]amine hydrochloride, A as prepared in Example A above (1.8 g, 8.3 mmol) was dissolved in methanol (100 ml) and 5% Pd/C (0.2 g) added. The mixture was stirred at room temperature, under 51 psi of hydrogen, for 2.5 hours (hydrogen uptake: AP=6.8 psi, calculated 7.1). The catalyst was removed by filtration and the solvent evaporated in vacuo. The residue was treated with ether (150 ml) and filtered to collect precipitate. The solid was dried at 45° C., in vacuo, overnight, to give 1.5 g (83%) of a white N-[(1,2-dihydro-1-acenaphthylenyl)methyl]amine hydrochloride salt, mp >250° C. Anal (C13H13N.HCl.0.15H2O), calc: C=71.20, H=6.48, N=6.30, Cl=15.54; found: C=70.14, H=6.51; N=6.42; Cl=16.11.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated in vacuo
  3. additionThe residue was treated with ether (150 ml)
  4. filtrationfiltered
  5. customto collect precipitate
  6. customThe solid was dried at 45° C., in vacuo, overnight

Sources & evidence

ORD record
ord-c2a659d3ea0445e1af623b42f00e9d73
Source dataset
uspto-grants-1987_06
Patent number
US04673670

Reaction notes

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