m-Chloroperbenzoic acid → 2-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)quinoline 1-oxide

HRID 1073960Notes

Reaction equation

HRID 1073960 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1([CH3:35])[CH:18]=[C:17]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)[C:16]2[CH:29]=[C:30]([C:33]#[N:34])[CH:31]=[CH:32][C:15]=2[O:14]1>ClCCl>[C:33]([C:30]1[CH:31]=[CH:32][C:15]2[O:14][C:13]([CH3:35])([CH3:12])[CH:18]=[C:17]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N+:20]=3[O-:9])[C:16]=2[CH:29]=1)#[N:34]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 198956232,2-dimethyl-4-(2-quinolyl)-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 198956762-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)quinoline 1-oxideYield 6.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

450 mg of m-chloroperbenzoic acid were added at room temperature to a solution of 624 mg of 2,2-dimethyl-4-(2-quinolyl)-2H-1-benzopyran-6-carbonitrile in 20 ml of dichloromethane. After stirring at room temperature for 6 hours the mixture was washed with sodium bicarbonate solution and the organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (4:1) for the elution and then chromatographed on silica gel a second time using methanol/ethyl acetate (1:9) for the elution. The product was recrystallized from toluene to give 45 mg of 2-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)quinoline 1-oxide of melting point 177° C.

Workup

  1. washwas washed with sodium bicarbonate solution
  2. dry with materialthe organic phase was dried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washfor the elution
  6. customchromatographed on silica gel a second time
  7. washfor the elution
  8. customThe product was recrystallized from toluene

Sources & evidence

ORD record
ord-49ae6f76b8aa42a097aa59c42717f759
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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