m-Chloroperbenzoic acid → HCID 21220527, compound

HRID 1584736Notes

Reaction equation

HRID 1584736 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]=[N:31][CH:30]=[CH:29][C:23]=4[CH2:24][CH2:25]3)=[N:20]2)=[CH:15][CH:14]=1>ClCCl>[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]=[N+:31]([O-:6])[CH:30]=[CH:29][C:23]=4[CH2:24][CH2:25]3)=[N:20]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21220546HCID 21220546, compound

Product 1

HCID 21220527HCID 21220527, compoundYield 72.1%

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[4,3-h]cinnoline (example 17, 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 (19 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-6b22efb7fc9944bba39a8407426f0b47
Source dataset
uspto-grants-1999_08
Patent number
US05935956

Reaction notes

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