m-Chloroperbenzoic acid → HCID 21220529, compound

HRID 1584737Notes

Reaction equation

HRID 1584737 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:28][CH2:27][CH:26]3[C:21]([C:22]4[CH:32]=[CH:31][CH:30]=[N:29][C:23]=4[CH2:24][CH2:25]3)=[N:20]2)=[CH:15][CH:14]=1>ClCCl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH2:28][CH2:27][CH:26]3[C:21]([C:22]4[CH:32]=[CH:31][CH:30]=[N+:29]([O-:6])[C:23]=4[CH2:24][CH2:25]3)=[N:20]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9796262HCID 9796262, compound

Product 1

HCID 21220529HCID 21220529, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Chloroperoxybenzoic acid (60%) (35 mg) was added to a solution of 2-(4-Chlorophenyl)-2,3,4,4a,5,6-hexahydropyrido[2,3-h]cinnoline (example 16, 25 mg) in dichloromethane (5 ml) at 25° C. After 4 hours the reaction was diluted with dichloromethane and sequentially washed with an aqueous solution of sodium metabisulfite, saturated sodium bicarbonate solution, brine, dried and evaporated. Purification by chromatography, eluting with ethyl acetate/methanol (4:1) afforded the title compound (17 mg).

Workup

  1. washsequentially washed with an aqueous solution of sodium metabisulfite, saturated sodium bicarbonate solution, brine
  2. customdried
  3. customevaporated
  4. customPurification by chromatography
  5. washeluting with ethyl acetate/methanol (4:1)

Sources & evidence

ORD record
ord-2035d50332e9449f91a031dd157dd351
Source dataset
uspto-grants-1999_08
Patent number
US05935956

Reaction notes

Loading…