Benzene → 3-Chloroisoquinoline 2-oxide

HRID 647425Notes

Reaction equation

HRID 647425 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.ClC1C=CC=C(C(OO)=[O:20])C=1.C1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[N+:3]([O-:20])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 241BenzeneHCID 70297m-Chloroperbenzoic acidHCID 6409683-Chloroisoquinoline

Product 1

HCID 122967123-Chloroisoquinoline 2-oxideYield 32.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-chloroisoquinoline (18.23 g), m-chloroperbenzoic acid (36.46 g) and benzene (180 ml) was stirred at ambient temperature for a period of 2.5 days. The mixture was diluted with dichloromethane and the resultant solution was washed several times with a aqueous 5% sodium bicarbonate solution and finally with water. The organic phase was dried over anhydrous magnesium sulfate and the solvent was evaporated to give a solid residue. The solid was recrystallised from ethyl acetate to give 3-chloroisoquinoline-2-oxide (6.53 g) as colourless crystals mp 147°-151° C.

Workup

  1. washthe resultant solution was washed several times with a aqueous 5% sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customto give a solid residue
  5. customThe solid was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-c2bd5873fdf742828d7718f0d9850fec
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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