m-Chloroperbenzoic acid → 5,6,7,8-Tetrahydro-4-methyl-8-(phenylsulphinyl)quinoline

HRID 1461282Notes

Reaction equation

HRID 1461282 reaction equation
[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([S:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[N:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:24]>ClCCl>[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([S:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:24])[C:6]=2[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 148359485,6,7,8-Tetrahydro-4-methyl-8-(phenylthio)quinoline

Product 1

HCID 148359495,6,7,8-Tetrahydro-4-methyl-8-(phenylsulphinyl)quinolineYield 101.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Step 4 (10.0 g, 39.2 mmol) in dichloromethane (200 ml) was treated portionwise with 86% 3-chloroperoxybenzoic acid (8.0 g, 40 mmol) at <10° , stirred for 30 min, washed with 0.1N-NaOH, dried (Na2SO4), and evaporated in vacuo to give the crude product (10.8 g) as a solid.

Workup

  1. washwashed with 0.1N-NaOH
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-20b889d085c0490aac2aae3642f3a19b
Source dataset
uspto-grants-1991_12
Patent number
US05075303

Reaction notes

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