HCID 20266005, compound → HCID 20266023, compound

HRID 1719861Notes

Reaction equation

HRID 1719861 reaction equation
[ClH:1].[CH2:2]([N:9]([CH2:14][CH:15]1[C:30](=[O:31])[C:19]2[C:20]3[CH2:21][CH2:22][C:23](=[O:29])[NH:24][C:25]=3[CH:26]=[C:27]([CH3:28])[C:18]=2[CH2:17][CH2:16]1)CCCC)[C:3]1C=CC=[CH:5][CH:4]=1>C(O)C.[Pd]>[OH2:29].[OH2:29].[ClH:1].[CH2:2]([NH:9][CH2:14][CH:15]1[C:30](=[O:31])[C:19]2[C:20]3[CH2:21][CH2:22][C:23](=[O:29])[NH:24][C:25]=3[CH:26]=[C:27]([CH3:28])[C:18]=2[CH2:17][CH2:16]1)[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 1

HCID 20266005HCID 20266005, compound

Product 1

HCID 20266023HCID 20266023, compoundYield 136.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

9(N-Benzyl-N-butylaminomethyl)-6-methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione hydrochloride (10 g) is dissolved in 300 ml of ethanol whereupon 2 g of 10% palladium-on-carbon is added, and the whole is kept under an atmosphere of hydrogen for 3 hours. The product partially crystallized out is dissolved well by adding methanol, and the catalyst is filtered off. The solvent is distilled off under reduced pressure, and the remaining crystals are recrystallized from ethanol to give 4.0 g of 9-butylaminomethyl-6-methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione hydrochloride dihydrate as colorless needles, melting at 194°-196° C.

Workup

  1. additionis added
  2. customThe product partially crystallized out
  3. dissolutionis dissolved well
  4. additionby adding methanol
  5. filtrationthe catalyst is filtered off
  6. distillationThe solvent is distilled off under reduced pressure
  7. customthe remaining crystals are recrystallized from ethanol

Sources & evidence

ORD record
ord-23caaf496f4342b9b67246838672b635
Source dataset
uspto-grants-1985_09
Patent number
US04543354

Reaction notes

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