m-Chloroperbenzoic acid → HCID 68933434, compound

HRID 2362508Notes

Reaction equation

HRID 2362508 reaction equation
[N:1]1([CH2:14][CH2:15][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1>>[O-:33][N+:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[C:13]2[N:1]([CH2:14][CH2:15][CH2:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:18])[CH:2]=[N:3][C:4]=2[CH:5]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68931340HCID 68931340, compound

Product 1

HCID 68933434HCID 68933434, compound

Procedure

The general method described in Steps 9 and 10 of Example 1 was used to aminate 4-(1H-imidazo[4,5-c]quinolin-1-yl)-1-phenylbutan-1-one (4.08 g, 12.9 mmol) by reaction with m-CPBA (3.20 g, 14.2 mmol) to provide 4-(5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-1-phenylbutan-1-one followed by reaction with p-toluenesulfonyl chloride (2.71 g, 14.2 mmol) and ammonium hydroxide solution (22 mL) to provide 4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)-1-phenylbutan-1-one) as white needles, mp 209-211° C.

Sources & evidence

ORD record
ord-b859b2f71351442a92c07917f9dee4f7
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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