HCID 13730343, compound → HCID 13730344, compound

HRID 65445Notes

Reaction equation

HRID 65445 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-1dc4bbdca16348a8a161085145f43291
Source dataset
uspto-grants-1986_09
Patent number
US04614732

Reaction notes

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