5,6-Dichloro-2-methylquinoline → 5,6-Dichloro-2-methyl-1,2,3,4-tetrahydroquinoline

HRID 1649429Notes

Reaction equation

HRID 1649429 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N:7]2.[H][H]>C(O)(=O)C.[Pt].[C]>[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([CH3:13])[NH:7]2

Participants

5

Reactant 2

HCID 155717745,6-Dichloro-2-methylquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 155717775,6-Dichloro-2-methyl-1,2,3,4-tetrahydroquinolineYield 78.5%

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

5,6-Dichloroquinaldine (5.5 g) was dissolved in 50 ml of acetic acid and 0.1 g of 5% platinum-carbon was added to the solution, which was then subjected to Parr's hydrogenation method to reduce the compound catalytically at a hydrogen gas pressure of 4 kg/cm2. After theoretical amount of hydrogen was absorbed the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. After rendering it alkaline with 50 ml of water and 20% sodium hydroxide, the residue was extracted with 100 ml of chloroform. The extract was dried by the addition of anhydrous potassium carbonate and concentrated to give 4.4 g of 5,6-dichloro-1,2,3,4-tetrahydroquinaldine as oily product.

Workup

  1. customAfter theoretical amount of hydrogen was absorbed the reaction mixture
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. extractionthe residue was extracted with 100 ml of chloroform
  5. dry with materialThe extract was dried by the addition of anhydrous potassium carbonate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a863ec653d7946b38de609a03582d909
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

Loading…