Hydrochloric Acid → HCID 68089435, compound

Temperature

0 °C

A mixture of N-(1-nitro-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide (800 mg, 3.88 mmol) in a 10 M solution of hydrochloric acid in MeOH were heated to reflux for 4 h. After concentration, the residue was basified with 2 N aqueous solution of NaOH to pH 9, then extracted with EtOAc (50 mL×2). The organic layer was washed with brine (30 mL), dried, and concentrated. The residue was dissolved in DMF (20 mL), cooled to 0° C., and NaH (60% dispersion in mineral oil, 0.155 mg, 3.88 mml) was added in one portion. Iodomethane (582 mg, 3.88 mmol) was added dropwise. The resulting mixture was stirred at the same temperature for another 2 h. The reaction mixture was quenched by ice (20 g) and then extracted with EtOAc (50 mL×2). The organic layer was washed with brine (20 mL), dried, and concentrated to give a yellow solid (190 mg). ESI MS: m/z 207 [M+H]+.

1. temperaturewere heated
2. temperatureto reflux for 4 h
3. concentrationAfter concentration
4. extractionextracted with EtOAc (50 mL×2)
5. washThe organic layer was washed with brine (30 mL)
6. customdried
7. concentrationconcentrated
8. dissolutionThe residue was dissolved in DMF (20 mL)
9. additionNaH (60% dispersion in mineral oil, 0.155 mg, 3.88 mml) was added in one portion
10. customThe reaction mixture was quenched by ice (20 g)
11. extractionextracted with EtOAc (50 mL×2)
12. washThe organic layer was washed with brine (20 mL)
13. customdried
14. concentrationconcentrated

ORD record

ord-0b0099d832274c369e15db0f175fd1d1

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765760B2