Hydrochloric Acid → HCID 67171636, compound

A mixture of 6-bromo-2-tetralone (1.00 g, 4.44 mmol) and methylamine hydrochloride (300 mg, 4.44 mol) in H2O (1 mL) and EtOH (1.5 mL) was stirred at ambient temperature for 20 min. Potassium cyanide (289 mg, 4.44 mmol) was added and stirring was continued for 18 h. The mixture was added dropwise to a stirred solution of 1.0 N aqueous HCl (4.5 mL) at 0° C., then potassium cyanate (360 mg, 4.44 mmol) was added portionwise. The stirred mixture was heated to 95° C. and conc. hydrochloric acid (0.44 mL) was added dropwise. The reaction mixture was heated at this temperature for 1 h, allowed to cool, and extracted with CH2Cl2 (80 mL). The organic extract was dried over Na2SO4, filtered, and concentrated to dryness. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 90:10 to provide a crude sample of the title compound (ca. 70% pure). Trituration with EtOH afforded the title compound as a pale solid. MS: m/z=311 (M+1).

1. stirringstirring
2. waitwas continued for 18 h
3. temperatureThe stirred mixture was heated to 95° C.
4. temperatureThe reaction mixture was heated at this temperature for 1 h
5. temperatureto cool
6. extractionextracted with CH2Cl2 (80 mL)
7. extractionThe organic extract
8. dry with materialwas dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated to dryness
11. customThe crude product was purified by silica gel chromatography
12. washeluting with a gradient of CH2Cl2

ORD record

ord-a2efebe5b18148a79a24e4342d4b25d2

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947678B2