Phenol → HCID 86640754, compound

Temperature

110 °C

A mixture of 9-chloroacridine (1.21 g, 5.7 mmol) and phenol (10.8 g, 57 mmol) was mixed and heated at 110° C. for 45 min under argon. Distilled ethylene diamine (3.4 g, 57 mmol) was added via syringe. After the reaction mixture was heated at 110° C. for additional 2 hrs, it was poured into 2N NaOH solution (60 mL). The product was extracted with ethyl ether (3×100 mL). The combined organic layer was washed with 2N NaOH solution (40 mL) and water (2×100 mL) and dried with anhydrous potassium carbonate. The solution was concentrated to 15 mL. Ethanol (15 mL) was added, followed by the addition of concentrated hydrochloric acid (10 mL). The mixture was cooled in freezer (−20° C.) for 4 hrs. The yellow solid formed was collected by centrifugation, washed with ethyl ether (10 mL) and dried under vacuum to provide Compound 7 as yellow powder 0.82 g (53%) which was used without any further purification. The structure of Compound 7 is given below:

1. additionwas mixed
2. temperatureAfter the reaction mixture was heated at 110° C. for additional 2 hrs
3. extractionThe product was extracted with ethyl ether (3×100 mL)
4. washThe combined organic layer was washed with 2N NaOH solution (40 mL) and water (2×100 mL)
5. dry with materialdried with anhydrous potassium carbonate
6. concentrationThe solution was concentrated to 15 mL
7. additionEthanol (15 mL) was added
8. additionfollowed by the addition of concentrated hydrochloric acid (10 mL)
9. temperatureThe mixture was cooled in freezer (−20° C.) for 4 hrs
10. customThe yellow solid formed
11. customwas collected by centrifugation
12. washwashed with ethyl ether (10 mL)
13. customdried under vacuum

ORD record

ord-4a616171de7b46d29a009f39bd460a40

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09250249B2