m-Chloroperbenzoic acid → 8,9,10,11-Tetrahydro[1,2]oxazepino[2',3':1,2]imidazo[4,5-c]quinoline 5-oxide

HRID 415512Notes

Reaction equation

HRID 415512 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][CH2:18][C:12]3=[N:11][C:4]=1[CH:5]=[N:6]2.ClC1C=C(C=CC=1)C(OO)=[O:24]>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][CH2:18][C:12]3=[N:11][C:4]=1[CH:5]=[N+:6]2[O-:24]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 666200338,9,10,11-Tetrahydro[1,2]oxazepino[2',3':1,2]imidazo[4,5-c]quinoline

Product 1

HCID 666199128,9,10,11-Tetrahydro[1,2]oxazepino[2',3':1,2]imidazo[4,5-c]quinoline 5-oxideYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 8,9,10,11-tetrahydro[1,2]oxazepino[2′,3′:1,2]imidazo[4,5-c]quinoline (0.1449 g, 0.605 mmol) in 6 mL of dichloromethane was treated with 3-chloroperoxybenzoic acid (0.30 g, 57-86% purity). After stirring for 40 minutes, the reaction mixture was diluted with dichloromethane, washed successively with dilute aqueous K2CO3, H2O, and brine, dried over Na2SO4, and concentrated under reduced pressure to give 0.1384 g of 8,9,10,11-tetrahydro[1,2]oxazepino[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-36d431cc2bfa4399bf84f5929d8f56a8
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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