Hydrochloric Acid → 2,3,6,7,8,9-Hexahydro-5-methyl(alpha-methylalanyl)aminomethylfuro-[2,3-f]quinoline-7-one

HRID 1900770Notes

Reaction equation

HRID 1900770 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]2[CH2:16][CH:15]([CH2:17][NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[NH2:21])[O:14][C:6]2=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH:9]=[CH:8]2.[H][H]>O.[Pd]>[CH3:2][C:3]1[CH:4]=[C:5]2[CH2:16][CH:15]([CH2:17][NH:18][C:19](=[O:24])[C:20]([CH3:22])([CH3:23])[NH2:21])[O:14][C:6]2=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9][CH2:8]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 233697105-Methyl-2-(alpha-methylalanyl)aminomethyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 867499952,3,6,7,8,9-Hexahydro-5-methyl(alpha-methylalanyl)aminomethylfuro-[2,3-f]quinoline-7-oneYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A hydrochloric acid salt of 5-methyl-2-(α-methylalanyl)aminomethyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (1.15 g, 3.27 mmol) was dissolved in water (30 ml). To the obtained solution, 10% palladium-on-carbon (1.15 g) was added, followed by stirring at 80° C. for 3.5 hours in the atmosphere of hydrogen. The reaction mixture was filtered, and the filtrate was condensed under reduced pressure. The resultant residue was subjected to a recrystallization procedure using methanol--ether to obtain 851 mg of the title compound as colorless powdery crystals (73.5%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customcondensed under reduced pressure
  3. customThe resultant residue was subjected to a recrystallization procedure

Sources & evidence

ORD record
ord-1f2c2a88dfc54b5a8bb0084a4b19bf38
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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