Isopropanol → 6-Methoxy-7-methylquinoline

Temperature

180 °C

1-methoxy-2-methyl-4-nitrobenzene (3A) (5 g, 30.0 mmol), 3-amino-1-propanol (0.57 mL, 7.5 mmol), isopropanol (3.43 mL, 4.5 mmol), ruthenium(III) chloride hydrate (156 mg, 0.75 mmol), triphenylphosphine (588 mg, 2.24 mmol), and tin(II) chloride dihydrate (1.69 g, 7.5 mmol) in dioxane/H2O (67 mL/7 mL) were placed in a stainless steel pressure vessel. After the system was flushed with argon, the mixture was stirred at 180° C. for 20 hours. The reaction mixture was filtered through a short silica gel column (ethyl acetate/chloroform mixture) to eliminate inorganic compounds and concentrated under reduced pressure. The organic layer was poured into saturated brine, extracted with chloroform, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residual oily material was separated by column chromatography to give the product 3B (200 mg, 15%). LCMS-ESI+ (m/z): 174.2 (M+H)+.

1. customAfter the system was flushed with argon
2. filtrationThe reaction mixture was filtered through a short silica gel column (ethyl acetate/chloroform mixture)
3. concentrationconcentrated under reduced pressure
4. additionThe organic layer was poured into saturated brine
5. extractionextracted with chloroform
6. dry with materialdried over anhydrous sodium sulfate
7. customevaporated under reduced pressure
8. customThe residual oily material was separated by column chromatography

ORD record

ord-777bcf34fd8e427ea76d87be20965b8e

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296758B2