m-Chloroperbenzoic acid → HCID 68932994, compound

HRID 521321Notes

Reaction equation

HRID 521321 reaction equation
[CH2:1]([O:3][CH:4]([O:23][CH2:24][CH3:25])[CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:9]=[C:8]1[CH2:20][CH2:21][CH3:22])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:34])C=1>>[CH2:24]([O:23][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N+:12]([O-:34])=[CH:11][C:10]=2[N:9]=[C:8]1[CH2:20][CH2:21][CH3:22])[CH3:25]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68933444HCID 68933444, compound

Product 1

HCID 68932994HCID 68932994, compound

Procedure

The general method described in Steps 9 and 10 of Example 1 was used to aminate 1-(3,3-diethoxyproyl)-2-propyl-1H-imidazo[4,5-c]quinoline (4.50 g, 13.2 mmol) by reaction with m-CPBA (5.3 g) to provide 1-(3,3-diethoxypropyl)-5-oxido-2-propyl-1H-imidazo[4,5-c]quinoline followed by reaction with p-toluenesulfonyl chloride (4.89 g, 25.7 mmol) and ammonium hydroxide solution (40 mL) to provide 1-(3,3-diethoxypropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as grey needles after recrystallization from methanol, mp 148-150° C.

Sources & evidence

ORD record
ord-9de151267df7458bae830b6759d6a73b
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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