Hydrochloric Acid → 6-Chloro-1,2,3,4-tetrahydroquinoline

HRID 1520166Notes

Reaction equation

HRID 1520166 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.Cl>C(O)C.O=[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 691636-Chloroquinoline

Product 1

HCID 111828396-Chloro-1,2,3,4-tetrahydroquinolineYield 78.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-chloroquinoline (1.5 g, 9.17 mmol) in C2H5OH (50 ml) was added PtO2 (41.5 mg, 0.18 mmol) and concentrated HCl (0.1 ml) under an atmosphere of hydrogen gas. The reaction was stirred overnight at room temperature, then concentrated in vacuo, diluted with water (100 ml), adjusted to pH 8 with aqueous sodium bicarbonate. The resulting solution was extracted with dichloromethane (3×80 ml) and the organic layers were combined, dried over anhydrous magnesium sulfate, concentrated in vacuo to afford 6-chloro-1,2,3,4-tetrahydroquinoline as a colorless oil (1.2 g, 78%).

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water (100 ml)
  3. extractionThe resulting solution was extracted with dichloromethane (3×80 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb941a698284415a9a1ee4380af89b77
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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