1,2,3,4,7,8-Hexahydroquinolin-5(6H)-one → HCID 13528240, compound

HRID 34650Notes

Reaction equation

HRID 34650 reaction equation
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH2:4][CH2:3][CH2:2]1.[H][H]>C(O)(=O)C.O=[Pt]=O>[NH:1]1[CH:10]2[CH:5]([CH:6]([OH:11])[CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 118159451,2,3,4,7,8-Hexahydroquinolin-5(6H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 13528240HCID 13528240, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

The procedure of Grob et al. (Helv. Chim. Acta 1965, 48, 799-808) was followed. A solution of 66.70 g (0.441 mol) of 2,3,4,6,7,8-hexahydro-5(1H)-quinolinone in 250 ml of glacial acetic acid containing 2 g of PtO2 was hydrogenated at 450 psi and 50° C. for 75 hours. Hydrogen uptake was only 57.2% of the theoretical. The sample was filtered, concentrated (to remove most of the acetic acid), cooled to 0° C., basified with 6N sodium hydroxide to a pH of 12 and extracted three times with 500 ml of methylene chloride. The combined methylene chloride extract was dried over magnesium sulfate, filtered and concentrated to give 24.80 g (36.2%) of decahydro-5-quinolinol, which was a three component isomeric mixture by gas chromatography (GC) analysis, as a light brown oily-solid. This mixture was carried on to the next step without further purification.

Workup

  1. filtrationThe sample was filtered
  2. concentrationconcentrated (
  3. customto remove most of the acetic acid),
  4. extractionextracted three times with 500 ml of methylene chloride
  5. extractionThe combined methylene chloride extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-aee2f85746d94991837e287a112028de
Source dataset
uspto-grants-1988_08
Patent number
US04762843

Reaction notes

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