HCID 19026188, compound → HCID 18409094, compound

HRID 1195159Notes

Reaction equation

HRID 1195159 reaction equation
[ClH:1].Cl.[CH3:3][C:4]1([NH2:22])[CH2:13][CH2:12][CH2:11][C:10]2[N:9]=[C:8]([O:14]CC3C=CC=CC=3)[CH:7]=[CH:6][C:5]1=2.[H][H]>C(O)C.[Pd]>[ClH:1].[NH2:22][C:4]1([CH3:3])[CH2:13][CH2:12][CH2:11][C:10]2[NH:9][C:8](=[O:14])[CH:7]=[CH:6][C:5]1=2

Participants

5

Reactant 2

HCID 19026188HCID 19026188, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 18409094HCID 18409094, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5,6,7,8-Tetrahydro-5-methyl-2-(phenylmethoxy)-5-quinolinamine dihydrochloride (9.5 g) and 10% palladium-on-carbon (730 mg) in absolute ethanol (500 ml) were shaken on a Parr hydrogenation apparatus, starting at 55 psi of hydrogen, until hydrogen uptake ceased. The catalyst was removed by filtration, and the filtrate was neutralized with 4-polyvinylpyridine and concentrated. The residue was suspended in hot methanol and the solid was collected. The solid was combined with the material that crystallized from the methanol to afford 3.36 g (56%) of product, mp 214°-216° C. (dec).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationconcentrated
  3. customthe solid was collected
  4. customthat crystallized from the methanol

Sources & evidence

ORD record
ord-baa4c5f0c61c4ab19a63e3458603be5d
Source dataset
uspto-grants-1992_05
Patent number
US05110815

Reaction notes

Loading…