Sodium Carbonate → 1-(2-Amino-6-chlorophenyl)ethanone

A suspension of 2-amino-6-chlorobenzonitrile (3.67 g, 24 mmol) in diethyl ether (60 ml) was added slowly to methylmagnesium bromide (56 ml, 3 M in Et2O, 170 mmol), and the mixture was heated to reflux, until all starting material was consumed (3 h, HPLC control). The mixture was then placed in an ice bath, and HCl (6M, 58 ml) was slowly added (vigorous reaction). The mixture was then again heated to reflux, cooled and made alkaline by addition of solid Na2CO3. The mixture was extracted several times with ethyl acetate, the combined organic phases were dried (Na2SO4), and the solvent was evaporated under reduced pressure. Purification of the residue by column chromatography (silica gel, solvent gradient n-heptan/ethyl acetate=100/0−60/40) gave the title compound (2.72 g, 67%). 1H NMR (CDCl3): δ 2.65 (3H, s), 4.91 (2H, bs), 6.58 (1H, d), 6.73 (1H, d), 7.07 (1H, t).

1. temperaturethe mixture was heated
2. temperatureto reflux, until all starting material
3. customwas consumed (3 h, HPLC control)
4. customThe mixture was then placed in an ice bath
5. additionHCl (6M, 58 ml) was slowly added
6. custom(vigorous reaction)
7. temperatureThe mixture was then again heated
8. temperatureto reflux
9. temperaturecooled
10. extractionThe mixture was extracted several times with ethyl acetate
11. dry with materialthe combined organic phases were dried (Na2SO4)
12. customthe solvent was evaporated under reduced pressure
13. customPurification of the residue by column chromatography (silica gel, solvent gradient n-heptan/ethyl acetate=100/0−60/40)

ORD record

ord-56f4bfc768f346da8d7dc14a5bd71d5d

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790732B2