m-Chloroperbenzoic acid → HCID 53949587, compound

HRID 892561Notes

Reaction equation

HRID 892561 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]3[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:12]=3[O:11][C:10]([CH3:21])([CH3:20])[CH:9]=2)=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>ClCCl>[C:18]([C:15]1[CH:16]=[CH:17][C:12]2[O:11][C:10]([CH3:21])([CH3:20])[CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][N+:6]=3[O-:30])[C:13]=2[CH:14]=1)#[N:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19895642HCID 19895642, compound

Product 1

HCID 53949587HCID 53949587, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

400 mg of 4-(5-hydroxy-2-pyridyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile and 350 mg of m-chloroperbenzoic acid were stirred overnight in 100 ml of dichloromethane. The mixture was washed in succession with sodium bisulphite solution, sodium bicarbonate solution and water, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using 10% (v/v) methanol/ ethyl acetate for the elution. There were obtained 30 mg of 2-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)-5-hydroxypyridine N-oxide of melting point 260°-262° C. (from ethanol).

Workup

  1. washThe mixture was washed in succession with sodium bisulphite solution, sodium bicarbonate solution and water
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel using 10% (v/v) methanol/ ethyl acetate for the elution

Sources & evidence

ORD record
ord-9328d9923bae44b5b7ee2216aebd1b2b
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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