m-Chloroperbenzoic acid → HCID 54264316, compound

HRID 892541Notes

Reaction equation

HRID 892541 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH: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])[CH2:9]2)[CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH: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])[CH2:9]2)[N+:7]=1[O-:30]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 19895637HCID 19895637, compound

Product 1

HCID 54264316HCID 54264316, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

152 mg of 4-(6-chloro-2-pyridyl)-3.4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile and 136 mg of m-chloroperbenzoic acid were heated at reflux in 15 ml of chloroform. After 10 hours and 20 hours 80 mg and 50 mg, respectively., of m-chloroperbenzoic acid were added. After 30 hours the mixture was allowed to cool to room temperature, washed in succession with sodium bisulphite solution and sodium bicarbonate solution, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate for the elution to give, after trituration with n-hexane, a solid which was recrystallized from acetonitrile. There were obtained 33 mg of 2-chloro-6-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide of melting point 195°-196° C.

Workup

  1. custom20 hours 80 mg and 50 mg
  2. waitAfter 30 hours the mixture was allowed
  3. washwashed in succession with sodium bisulphite solution and sodium bicarbonate solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution
  8. customto give
  9. customafter trituration with n-hexane, a solid which was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-da27bbdee48f45d3b0b9abb04aaef2c8
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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