5,6,7,8-Tetrahydro-4-methyl-8-(phenylsulphinyl)quinoline → 4-Methyl-5,6-dihydroquinoline

HRID 1461283Notes

Reaction equation

HRID 1461283 reaction equation
[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7](S(C3C=CC=CC=3)=O)[C:6]=2[N:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8]=[CH:7][C:6]=2[N:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 148359495,6,7,8-Tetrahydro-4-methyl-8-(phenylsulphinyl)quinoline

Product 1

HCID 121336204-Methyl-5,6-dihydroquinolineYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The crude product of Step 5 (10.8 g, 40.0 mmol) was heated under reflux in toluene (100 m) for 30 min, cooled to room temperature, and extracted with 1N-HCl (3×50 ml). The extracts were basified with 10N-NaOH and extracted with dichloromethane (3×200 ml). The organic extracts were dried (MgSO4) and evaporated in vacuo to give an oil which was purified by chromatography (alumina; ether) to give the product (5.5 g, 95%) as an oil.

Workup

  1. extractionextracted with 1N-HCl (3×50 ml)
  2. extractionextracted with dichloromethane (3×200 ml)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. customevaporated in vacuo
  5. customto give an oil which
  6. customwas purified by chromatography (alumina; ether)

Sources & evidence

ORD record
ord-2ec8f732fb6d4bfa9da7b3865620022f
Source dataset
uspto-grants-1991_12
Patent number
US05075303

Reaction notes

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