m-Chloroperbenzoic acid → HCID 19738137, compound

HRID 2255427Notes

Reaction equation

HRID 2255427 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1.ClC1C=C(C=CC=1)C(OO)=[O:26]>C(Cl)Cl>[Cl:15][C:11]1[CH:10]=[C:9]2[C:14]([C:5]([O:4][C:3]3[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:2]=3[Cl:1])=[CH:6][CH:7]=[N+:8]2[O-:26])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19738145HCID 19738145, compound

Product 1

HCID 19738137HCID 19738137, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5.0 g (16.22 mmol) of 4-(2-chloro-4-fluorophenoxy)-7-chloroquinoline, 4.20 g (19.47 mmol) of 80% 3-chloroperoxybenzoic acid, and 50 ml of CH2Cl2 was stirred at 0° C. for six hours. The CH2Cl2 was removed by reducing pressure, and the residue was dissolved in ethyl acetate and washed with base. After removing solvent from the organic layer by reducing pressure, a white solid formed. This was recrystallized in ethyl acetate. Yield 3.04 g (58%). M.P. 177°-178° C.

Workup

  1. customThe CH2Cl2 was removed
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with base
  4. customAfter removing solvent from the organic layer
  5. customa white solid formed
  6. customThis was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-a36587497b6e4b92a5c6d2f744a67ce2
Source dataset
uspto-grants-1993_08
Patent number
US05240940

Reaction notes

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