m-Chloroperbenzoic acid → HCID 68938533, compound

HRID 521323Notes

Reaction equation

HRID 521323 reaction equation
[CH3:1][C:2]([CH3:24])([CH2:17][C:18]1([CH3:23])[O:22][CH2:21][CH2:20][O:19]1)[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[CH:5]1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1>>[CH3:1][C:2]([CH3:24])([CH2:17][C:18]1([CH3:23])[O:22][CH2:21][CH2:20][O:19]1)[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N+:9]([O-:33])=[CH:8][C:7]=2[N:6]=[CH:5]1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68928912HCID 68928912, compound

Product 1

HCID 68938533HCID 68938533, compound

Procedure

The general method described in Steps 9 and 10 of Example 1 was used to aminate 1-[2,2-dimethyl-3-(2-methyl[1,3]dioxolan-2-yl)propyl]-1H-imidazo[4,5-c]quinoline (8.8 g, 27 mmol) by reaction with m-CPBA (11.8 g) to provide 1-[2,2-dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)propyl]-5-oxido-1H-imidazo[4,5-c]quinoline followed by reaction with p-toluenesulfonyl chloride (9.1 g, 48 mmol) and ammonium hydroxide solution (100 mL) to provide 1-[2,2-dimethyl-3-(2-methyl[1,3]dioxolan-2-yl)propyl]-1H-imidazo[4,5-c]quinolin-4-amine as a light brown solid after chromatography on silica gel (elution with a solution of 7% methanol in dichloromethane that contained about 5 mL of ammonium hydroxide solution per liter of eluent) and recrystallization from aqueous methanol, mp 153-155° C.

Sources & evidence

ORD record
ord-ae83acfaea8f44bc81189ff35a1260d3
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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