m-Chloroperbenzoic acid → HCID 178423754, compound

HRID 892545Notes

Reaction equation

HRID 892545 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[NH2:12][C:13]1[N:18]=[C:17]([C:19]2[C:24]3[CH:25]=[C:26]([C:29]#[N:30])[CH:27]=[CH:28][C:23]=3[O:22][C:21]([CH3:32])([CH3:31])[CH:20]=2)[CH:16]=[CH:15][CH:14]=1>ClCCl>[NH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([C:19]2[C:24]3[CH:25]=[C:26]([C:29]#[N:30])[CH:27]=[CH:28][C:23]=3[O:22][C:21]([CH3:32])([CH3:31])[CH:20]=2)[N+:18]=1[O-:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19895661HCID 19895661, compound

Product 1

HCID 178423754HCID 178423754, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

406 mg of m-chloroperbenzoic acid were added to a solution of 554 mg of 4-(6-amino-2-pyridyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile in 10 ml of dichloromethane and the mixture was stirred for 3 hours. The mixture was then washed with sodium bicarbonate solution, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using methanol/ethyl acetate (1:4) for the elution to give a solid which was triturated with dichloromethane and recrystallized from isopropanol. There were obtained 130 mg of 2-amino-6-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide of melting point 241°-242° C.

Workup

  1. washThe mixture was then washed with sodium bicarbonate solution
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washfor the elution
  6. customto give a solid which
  7. customwas triturated with dichloromethane
  8. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-cb59c355c3294df6a2b9ed36d99f66ad
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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