m-Chloroperbenzoic acid → HCID 68931850, compound

HRID 521298Notes

Reaction equation

HRID 521298 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][C:20](=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C1C=C(Cl)C=C(C(OO)=[O:36])C=1>>[O-:36][N+:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[C:6]2[N:5]([CH2:17][CH2:18][CH2:19][C:20](=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]([CH2:1][CH2:2][CH3:3])=[N:16][C:7]=2[CH:8]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57455403HCID 57455403, compound

Product 1

HCID 68931850HCID 68931850, compound

Procedure

The general method described in Steps 9 and 10 of Example 1 was used to aminate 1-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)decan-4-one (6.10 g, 17.2 mmol) by reaction with m-CPBA (8.50 g) to provide 1-(5-oxido-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)decan-4-one followed by reaction with p-toluenesulfonyl chloride (4.90 g, 25.8 mmol) and ammonium hydroxide solution (100 mL) to provide 1-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)decan-4-one) as a white solid after recrystallization from aqueous methanol, mp 111-113° C.

Sources & evidence

ORD record
ord-2562411c9dfb4804a813d8e9952fac54
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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