Acetone → N-(2-Butyl-1H-imidazo[4,5-c]quinolin-1-yl)propan-2-imine

HRID 1373885Notes

Reaction equation

Cl.[CH2:2]([C:6]1[N:7]([NH2:19])[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH2:3][CH2:4][CH3:5].[CH3:20][C:21]([CH3:23])=O>C(O)(C)C>[CH2:2]([C:6]1[N:7]([N:19]=[C:21]([CH3:23])[CH3:20])[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 2-butyl-1H-imidazo[4,5-c]quinolin-1-amine hydrochloride (520 mg, 2.17 mmol) in 10 mL of isopropanol was treated with 2 mL of acetone and 200 mg of DOWEX W50-X1 acid resin. The reaction mixture was heated to 55° C. overnight. The reaction mixture was treated with an additional 10 mL of isopropanol and 5 mL of acetone and heated to 70° C. for 2 h. The reaction mixture was filtered and the filtrate was treated with 0.5 mL of triethylamine and concentrated under reduced pressure. Chromatography (SiO2, 3% MeOH/CHCl3) gave N-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine (421 mg) as a brown oil.

Workup

temperatureheated to 70° C. for 2 h
filtrationThe reaction mixture was filtered
additionthe filtrate was treated with 0.5 mL of triethylamine
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d14717eb205e43c98c6ee0c6d5b98df2
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163947B2

Reaction notes

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