Tetrahydrofuran → HCID 22175327, compound

Temperature

-78 °C

To a solution of dimethyl sulfoxide;(1.7 ml, 24 mmol) in tetrahydrofuran (10 mmol) was added oxalyl chloride (1.05 ml, 12 mmol) at −78° C. and the obtained mixture was stirred at −78° C. for 15 min. To the mixture was added 4-butoxy-6,7-dichloro-3-hydroxymethyl-2-methyl-1(2H)-isoquinolinone (synthesized according to the method similar to that in Example 36 (3)) (2.43 g, 5mmol) and the obtained mixture was stirred at −78° C. for 5 min. To the mixture was added triethylamine (5.6 ml, 40mmol) and the obtained mixture was stirred at room temperature for 30 min. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from tetrahydrofuran-diisopropyl ether to give 4-butoxy-6,7-dichloro-2-methyl-1-oxo-1,2-dihydro-3-isoquinolinealdehyde (2.14 g, 81.7%) as crystals.

1. customsynthesized
2. stirringthe obtained mixture was stirred at −78° C. for 5 min
3. stirringthe obtained mixture was stirred at room temperature for 30 min
4. extractionextracted with ethyl acetate
5. washThe extract was washed with brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was recrystallized from tetrahydrofuran-diisopropyl ether

ORD record

ord-4dcc6b1f5e654d1f88abb40ab65e20de

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07034039B2