m-Chloroperbenzoic acid → HCID 69431609, compound

HRID 1373066Notes

Reaction equation

HRID 1373066 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6]([CH:14]=[CH2:15])=[CH:7][N:8]=[CH:9]2)([O-:3])=[O:2].ClC1C=CC=C(C(OO)=[O:24])C=1.C(=O)([O-])O.[Na+]>ClCCl>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6]([CH:14]=[CH2:15])=[CH:7][N+:8]([O-:24])=[CH:9]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 23112184HCID 23112184, compound

Product 1

HCID 69431609HCID 69431609, compoundYield 108.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 5-nitro-4-vinylisoquinoline (23 g) obtained in Step A mentioned above was dissolved in dichloromethane (400 ml), then slowly added with m-chloroperbenzoic acid (43 g, Tokyo Kasei Kogyo), and stirred for 3.5 hours. The reaction mixture was cooled on ice, and then neutralized by addition of saturated aqueous sodium hydrogencarbonate. Then, the organic layer was separated, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound (27 g).

Workup

  1. temperatureThe reaction mixture was cooled on ice
  2. customThen, the organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4131a6bcd10a4e838c78587d7e182dc6
Source dataset
uspto-grants-2007_01
Patent number
US07160894B2

Reaction notes

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