Methanol → HCID 178499073, compound

Temperature

60 °C

To a stirred solution of compound of example 1 (0.30 g, 1.97 mmol) in methanol (10 mL) was added dimethyl acetylenedicarboxylate (0.34 g, 2.36 mmol) and the reaction mixture was heated at 60° C. for 4 hours. Methanol was removed under reduced pressure and xylene (20 mL) was added to the reaction mixture and heated at 140° C. for 12 hours. The reaction mixture was then concentrated, and residue obtained was dissolved in 5% aqueous NaOH (20 mL) and was washed with ethyl acetate (2×50 mL) to remove unreacted organic impurities. Aqueous layer was then acidified with dilute 10% acetic acid, extracted with ethyl acetate (3×50 mL), dried over anhydrous sodium sulfate and concentrated to obtain the title compound.

1. customMethanol was removed under reduced pressure and xylene (20 mL)
2. additionwas added to the reaction mixture
3. temperatureheated at 140° C. for 12 hours
4. concentrationThe reaction mixture was then concentrated
5. customresidue obtained
6. washwas washed with ethyl acetate (2×50 mL)
7. customto remove unreacted organic impurities
8. additionwith dilute 10% acetic acid
9. extractionextracted with ethyl acetate (3×50 mL)
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated

ORD record

ord-3ca1adf2ef67489d8cc50c7c4f4512b6

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314103B2