m-Chloroperbenzoic acid → HCID 19895688, compound

HRID 892559Notes

Reaction equation

HRID 892559 reaction equation
[NH2:1][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.[Cl:22]C1C=CC=C(C(OO)=[O:30])C=1>ClCCl>[ClH:22].[NH2:1][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]([O-:30])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 19895584HCID 19895584, compound

Product 1

HCID 19895688HCID 19895688, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g of 4-(5-amino-2-pyridyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile was dissolved in 15 ml of dichloromethane and 1 g of m-chloroperbenzoic acid was added. After stirring at room temperature for 1 hour a further 0.5 g of m-chloroperbenzoic acid was added. After stirring at room temperature overnight 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 firstly 10% (v/v) methanol/ethyl acetate and then 20% (v/v) methanol/ethyl acetate for the elution. The product, 5-amino-2-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)-pyridine, was converted into the hydrochloride salt which was recrystallized from isopropanoI. There were obtained 238 mg of 5-amino-2-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide hydrochloride of melting point 235°-237° C.

Workup

  1. additionwas added
  2. washwas washed in succession with sodium bisulphite solution, sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel using firstly 10% (v/v) methanol/ethyl acetate
  6. wash20% (v/v) methanol/ethyl acetate for the elution
  7. customwas recrystallized from isopropanoI

Sources & evidence

ORD record
ord-3b85e9220ddc4d3eb308a4d8b6752eb5
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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