m-Chloroperbenzoic acid → HCID 15790213, compound

HRID 2399675Notes

Reaction equation

HRID 2399675 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=3[Cl:21])[C:6]=2[CH:5]=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)(Cl)Cl.ClCCl>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:20])[F:19])=[CH:13][C:12]=3[Cl:21])[C:6]=2[CH:5]=[CH:4][N+:3]=1[O-:30]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 15790212HCID 15790212, compound

Product 1

HCID 15790213HCID 15790213, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

4-chloro-1-(2'-chloro-4'-trifluoromethylphenyl)-pyrrolo[3,2-c]pyridine (1.10 g, 33 mmol) and meta-chloroperbenzoic acid (approximately 80-85%, 1.15 g) were stirred together in chloroform (20 ml) at room temperature overnight. A further quantity of meta-chloroperbenzoic acid (1.15 g) was added, and stirring continued for 2 hours. The mixture was diluted with dichloromethane and washed with saturated aqueous sodium carbonate solution. The organic portion was dried over magnesium sulfate, filtered, and the filtrate evaporated in vacuo. The residue was triturated with hexane to give 4-chloro-1-(2'-chloro-4'-trifluoromethylphenyl)-pyrrolo[3,2-c]-pyridine 5-oxide (0.69 g) as a tan solid, m.p. 119°-123° C. (with dec.)

Workup

  1. washwashed with saturated aqueous sodium carbonate solution
  2. dry with materialThe organic portion was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe filtrate evaporated in vacuo
  5. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-6b55b5ab6d06402794cea5b2a0c287b7
Source dataset
uspto-grants-1995_09
Patent number
US05451566

Reaction notes

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