Dimethyl Sulfoxide → 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butanal
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([C:13]1[N:14]([CH2:26][CH2:27][CH2:28][CH2:29][OH:30])[C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:25]=1)[CH3:12].C(N(CC)CC)C>ClCCl>[CH2:11]([C:13]1[N:14]([CH2:26][CH2:27][CH2:28][CH:29]=[O:30])[C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:25]=1)[CH3:12]Participants
Procedure
Under a nitrogen atmosphere, dimethylsulfoxide (3.6 mL, 1.5 eq.) and oxalyl chloride (3.5 mL, 1.1 eq.) were sequentially added dropwise to chilled (dry ice/acetone bath) dichloromethane (100 mL). A solution of 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol (10 g, 37 mmol, 1 eq.) in dichloromethane was added dropwise. Triethylamine (15.5 mL, 3 eq.) was added. The ice bath was removed and the reaction mixture was allowed to warm to ambient temperature. After about 2 hours analysis by TLC indicated that the reaction was complete. The reaction mixture was diluted with dichloromethane (175 mL) and water (200 mL) and made basic (pH 10) with aqueous 5% sodium carbonate. The organic layer was washed sequentially with water (2×200 mL) and brine (150 mL) and then concentrated under reduced pressure to provide 9.9 g of 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butanal.
Workup
- customThe ice bath was removed
- additionThe reaction mixture was diluted with dichloromethane (175 mL) and water (200 mL)
- washThe organic layer was washed sequentially with water (2×200 mL) and brine (150 mL)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-a7310def4c1848dea55c9d98d05de177
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802853B2
Reaction notes
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