m-Chloroperbenzoic acid → HCID 66619891, compound

HRID 415507Notes

Reaction equation

HRID 415507 reaction equation
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:13]3[O:14][CH2:15][CH2:16][CH2:17][C:12]3=[N:11][C:4]=1[CH:5]=[N:6]2.ClC1C=C(C=CC=1)C(OO)=[O:23]>ClCCl>[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:13]3[O:14][CH2:15][CH2:16][CH2:17][C:12]3=[N:11][C:4]=1[CH:5]=[N+:6]2[O-:23]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66619870HCID 66619870, compound

Product 1

HCID 66619891HCID 66619891, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

9,10-Dihydro-8H-[1,2]oxazino[2′,3′:1,2]imidazo[4,5-c]quinoline (0.3339 g, 1.482 mmol) was dissolved in 5 mL of dichloromethane and treated with 3-chloroperoxybenzoic acid (0.95 g, 57-86% purity). After stirring for 1 hour, the reaction mixture was diluted with 15 mL of dichloromethane, washed successively with dilute aqueous K2CO3, H2O, and brine, dried over Na2SO4, and concentrated under reduced pressure to give 0.364 g of 9,10-dihydro-8H-[1,2]oxazino[2′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide as a tan solid.

Workup

  1. washwashed successively with dilute aqueous K2CO3, H2O, and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa7f6f24500948ac8bad4993b001ebdb
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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