Dichloromethane → HCID 59497129, compound

To a 500 mL round-bottomed flask equipped with a reflux condenser containing 2-methyl-[1,10]phenathrolin-4-ol, (10.20 g, 48.5 mmol), was slowly added phosphorus oxychloride (200 mL) and the mixture was refluxed for 3 hours. The reaction flask was allowed to cool down to room temperature and the solvent was removed in a rotary evaporator. The solid obtained was treated with methylene chloride (200 mL) and saturated NaHCO3 (200 mL) and transferred to a separatory funnel. The aqueous layer was further extracted with methylene chloride (200 mL) and the combined organic layers were washed with brine (200 mL), dried (Na2SO4), filtered and concentrated. The residue obtained was treated with ethyl ether (100 mL), filtered and dried yielding a light brown solid (9.00 g). A second crop of 0.60 g of material was obtained from the mother liquors as a light yellow solid, with an overall yield of 9.60 g (87% yield).

1. customTo a 500 mL round-bottomed flask equipped with a reflux condenser
2. temperaturethe mixture was refluxed for 3 hours
3. customthe solvent was removed in a rotary evaporator
4. customThe solid obtained
5. customtransferred to a separatory funnel
6. extractionThe aqueous layer was further extracted with methylene chloride (200 mL)
7. washthe combined organic layers were washed with brine (200 mL)
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue obtained
12. filtrationfiltered
13. customdried

ORD record

ord-aba6d4fcc4e54169b3b3f78b1808fb2c

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592446B2