Thionyl Chloride → HCID 86656163, compound

To a mixture of 8-hydroxyquinoline-7-carboxylic acid (5.0 g, 26 mmol, TCI America) in methylene chloride (50 mL) was added thionyl chloride (4.24 mL, 58.1 mmol). After stirred at room temperature overnight, the mixture was concentrated to dryness under reduced pressure. The residue was exposed to high vacuum then mixed with tetrahydrofuran (50 mL). To the resultant mixture was added N,O-dimethylhydroxylamine hydrochloride (3.09 g, 31.7 mmol) followed by N,N-diisopropylethylamine (13.8 mL, 79.3 mmol). The reaction was heated at 50° C. overnight, then cooled and quenched with water, and extracted with dichloromethane. The combined organic layers were washed with water, brine and dried over sodium sulfate. After evaporated to dryness, the residue was purified on silica gel, eluting with 0 to 10% methanol in dichloromethane, to give the desired product (4.09 g, 66%). LCMS calculated for C12H13N2O3(M+H)+: m/z=233.1; found: 233.0.

1. concentrationthe mixture was concentrated to dryness under reduced pressure
2. additionthen mixed with tetrahydrofuran (50 mL)
3. temperatureThe reaction was heated at 50° C. overnight
4. temperaturecooled
5. customquenched with water
6. extractionextracted with dichloromethane
7. washThe combined organic layers were washed with water, brine
8. dry with materialdried over sodium sulfate
9. customAfter evaporated to dryness
10. customthe residue was purified on silica gel
11. washeluting with 0 to 10% methanol in dichloromethane

ORD record

ord-651a39e078a64bc8beba2a16ea898f4b

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680108B2