Reaction #9556

Reaction equation

1-(3-amino-7-benzylquinolin-4-ylamino)-2-methylpropan-2-ol

1-(3-amino-6-benzylquinolin-4-ylamino)-2-methylpropan-2-ol

triethyl orthoformate

→

1-(7-benzyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

1-(8-benzyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Conditions

Workup

1. 1
   TemperatureThe reaction was heated
2. 2
   Temperatureat reflux for one hour
3. 3
   OtherA precipitate formed
4. 4
   Otherwhich was isolated by filtration

Procedure

For Examples 431 and 434, a modification of the method described in Part B of Examples 427–429 was used to treat 1-(3-amino-7-benzylquinolin-4-ylamino)-2-methylpropan-2-ol or 1-(3-amino-6-benzylquinolin-4-ylamino)-2-methylpropan-2-ol with triethyl orthoformate, as indicated in the table below. The reaction was heated at reflux for one hour and then stirred overnight at ambient temperature. A precipitate formed, which was isolated by filtration to provide 1-(7-benzyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol or 1-(8-benzyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.

Source