2-butyl-1-isobutyl-7-[(E)-2-phenylethenyl]-1H-imidazo[4,5-c]quinolin-4-amine → 2-butyl-1-isobutyl-7-phenethyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9356Notes

Reaction equation

HRID 9356 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:7]2[C:16]3[CH:15]=[CH:14][C:13](/[CH:17]=[CH:18]/[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:12][C:11]=3[N:10]=[C:9]([NH2:25])[C:8]=2[N:26]=1)[CH2:2][CH2:3][CH3:4]>[Pd]>[CH2:1]([C:5]1[N:6]([CH2:27][CH:28]([CH3:29])[CH3:30])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([CH2:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:12][C:11]=3[N:10]=[C:9]([NH2:25])[C:8]=2[N:26]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 219841252-butyl-1-isobutyl-7-[(E)-2-phenylethenyl]-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 219840602-butyl-1-isobutyl-7-phenethyl-1H-imidazo[4,5-c]quinolin-4-amineYield 26.6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2-Butyl-1-isobutyl-7-[(E)-2-phenylethenyl]-1H-imidazo[4,5-c]quinolin-4-amine (562 mg, 1.41 mmol) was hydrogenated in a Parr bottle over palladium on carbon (10%) until the starting material was consumed as judged by high performance liquid chromatography (HPLC) and thin layer chromatography (TLC) analyses. Purification on silica (5% to 10% methanol in CH2Cl2 gradient) followed by recrystallization from boiling CH3CN afforded 150 mg of 2-butyl-1-isobutyl-7-phenethyl-1H-imidazo[4,5-c]quinolin-4-amine, m.p. 181–182° C.

Workup

  1. customwas consumed
  2. customPurification on silica (5% to 10% methanol in CH2Cl2 gradient)
  3. customfollowed by recrystallization

Sources & evidence

ORD record
ord-a10c8fa6f2f44d2892a4bdf1b6af3582
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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