m-Chloroperbenzoic acid → HCID 67505829, compound

HRID 2105505Notes

Reaction equation

HRID 2105505 reaction equation
[CH2:1]([C:5]1[N:6]([O:18][CH:19]([CH3:21])[CH3:20])[C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4].ClC1C=C(C=CC=1)C(OO)=[O:27].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([C:5]1[N:6]([O:18][CH:19]([CH3:20])[CH3:21])[C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-:27])=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67505846HCID 67505846, compound

Product 1

HCID 67505829HCID 67505829, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-butyl-1-isopropoxy-1H-imidazo[4,5-c][1,5]naphthyridine (0.40 g, 1.4 mmol) in dichloromethane (25 mL) was cooled to approximately 0° C., and 3-chloroperoxybenzoic acid (0.42 g of approximately 77% pure material, 1.9 mmol) was added. The reaction was stirred for ten minutes at 0° C., stirred for 1.5 hours at room temperature, and then stirred with saturated aqueous sodium bicarbonate (25 mL) for 15 minutes. The organic layer was separated and dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 0.42 g of 2-butyl-1-isopropoxy-5-oxido-1H-imidazo[4,5-c][1,5]naphthyridine as a yellow oil.

Workup

  1. stirringstirred for 1.5 hours at room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40f1b61f4dc943f4ae6fb9be3948a82f
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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