m-Chloroperbenzoic acid → HCID 68934027, compound

HRID 521318Notes

Reaction equation

HRID 521318 reaction equation
[CH2:1]([O:3][CH:4]([O:22][CH2:23][CH3:24])[CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=[C:7]1[CH2:19][CH2:20][CH3:21])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:33])C=1>>[CH2:1]([O:3][CH:4]([O:22][CH2:23][CH3:24])[CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N+:11]([O-:33])=[CH:10][C:9]=2[N:8]=[C:7]1[CH2:19][CH2:20][CH3:21])[CH3:2]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68933325HCID 68933325, compound

Product 1

HCID 68934027HCID 68934027, compound

Procedure

The general method described in Steps 9 and 10 of Example 1 was used to aminate 1-(2,2-diethoxyethyl)-2-propyl-1H-imidazo[4,5-c]quinoline (4.50 g, 13.7 mmol) by reaction with m-CPBA (6.0 g) to provide 1-(2,2-diethoxyethyl)-5-oxido-2-propyl-1H-imidazo[4,5-c]quinoline followed by reaction with p-toluenesulfonyl chloride (4.60 g, 24.1 mmol) and ammonium hydroxide solution (130 mL) to provide 1-(2,2-diethoxyethyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid after recrystallization from aqueous methanol, mp 148-150° C.

Sources & evidence

ORD record
ord-7fe0b6a6cec6407aacc34deb5ba4f969
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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