m-Chloroperbenzoic acid → 4-Benzenesulfinyl-6,7-dimethoxy-quinoline

HRID 2115769Notes

Reaction equation

HRID 2115769 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.ClC1C=C(C=CC=1)C(OO)=[O:27].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:16]1([S:15]([C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[O:27])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67520293HCID 67520293, compound

Product 1

HCID 675205384-Benzenesulfinyl-6,7-dimethoxy-quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 6,7-dimethoxy-4-phenylsulfanyl-quinoline (Step a, 1.0 g, 3.4 mmol) in CH2Cl2 (30 mL) at −78° C., 3-chloroperoxybenzoic acid (0.64 g, 3.7 mmol) was added in CH2Cl2 dropwise slowly. The reaction was stirred at −78° C. for 2 h. The solution was poured into saturated NaHCO3 and extracted with CH2Cl2 3×. The combined organic layer was washed with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography with (70-100% EtOAc/Hexane) to give the titled compound as a white solid. MS (ESI, pos. ion) m/z: 314.4 (M+1).

Workup

  1. extractionextracted with CH2Cl2 3×
  2. washThe combined organic layer was washed with saturated NaHCO3, water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel column chromatography with (70-100% EtOAc/Hexane)

Sources & evidence

ORD record
ord-e42c2274ad05476885ea43dcdd94a3f9
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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