m-Chloroperbenzoic acid → HCID 22992260, compound

HRID 1168384Notes

Reaction equation

HRID 1168384 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([O:14][CH2:15][C:16]1[N:17]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:28]=1)[CH3:13].[Al]>C(Cl)(Cl)Cl>[CH2:12]([O:14][CH2:15][C:16]1[N:17]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N+:21]([O-:9])=[CH:20][C:19]=2[N:28]=1)[CH3:13]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 5359268AluminumHCID 22172705HCID 22172705, compound

Product 1

HCID 22992260HCID 22992260, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloroperbenzoic acid (3.7 g, 13.4 mmol) was added in 3 portions to a solution of 2-ethoxymethyl-1-phenylmethyl-1H-imidazo[4,5-c][1,5]naphthyridine (3.9 g, 12.2 mmol) in chloroform (100 mL) in a flask covered with aluminum foil. The reaction mixture was stirred at ambient temperature overnight; and then it was washed twice with dilute aqueous sodium bicarbonate and once with brine. The chloroform layer was divided into two portions. One portion was used in the example below. The second portion was concentrated under vacuum. The residue was recrystallized from isopropyl alcohol to provide 2-ethoxymethyl-1-phenylmethyl-1H-imidazo[4,5-c][1,5]naphthyridine-5-oxide as a solid, m.p. 187.5-189° C. Analysis: Calculated for C19H18N4O2+¼ H2O: %C, 67.52; %H, 5.49; %N, 16.58; Found: %C, 67.56; %H, 5.36; %N, 16.77.

Workup

  1. washand then it was washed twice with dilute aqueous sodium bicarbonate and once with brine
  2. concentrationThe second portion was concentrated under vacuum
  3. customThe residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-9a1be3ed713c4bfe86907574919bcbd3
Source dataset
uspto-grants-2003_09
Patent number
US06624172B2

Reaction notes

Loading…