Acetaldehyde → alpha-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methanol

HRID 991911Notes

Reaction equation

[CH3:1][CH:2]([CH3:17])[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.[CH:18](=[O:20])[CH3:19]>>[CH3:19][CH:18]([C:5]1[N:4]([CH2:3][CH:2]([CH3:17])[CH3:1])[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]=1)[OH:20]

Participants

Reactant 2

HCID 177Acetaldehyde

HCID 11424651Deaminoimiquimod

Product 1

HCID 15224403alpha-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methanol

Procedure

Using the general method of Example 45, 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (20 g; 89 mmol) was reacted with acetaldehyde to provide the desired product. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Sources & evidence

ORD record: ord-83febce531184ae9ab086bf8d81bd940
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465654B2

Reaction notes

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