Hydrochloric Acid → 1-(2-Amino-5-chlorophenyl)-2,2,2-trifluoroethanone

6N Hydrochloric acid (6.0M, 257 mmol) was added to N-[4-chloro-2-(trifluoroacetyl)phenyl]-2,2-dimethylpropanamide (3.3 g, 10.7 mmol) in anhydrous dimethoxyethane (40 ml) at room temperature and mixture was heated to reflux conditions for two hours until no starting material was observed by LC/MS. After cooling reaction to 0° C., reaction was basified to pH 9 by adding solid sodium bicarbonate in portions. Reaction was extracted with ethyl acetate (3×150 ml), and combined organic extracts were dried over MgSO4 and Na2SO4. After filtering mixture, the collected filtrate was concentrated in vacuo to give a crude yellow solid. Flash chromatography of the crude solid on silica gel (0-25% ethyl acetate/hexanes) afforded 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 7.70 (m, 1H), 7.32 (dd, J=2.4 and 9.2 Hz, 1H), 6.68 (d, J=8.8 Hz, 1H), 6.46 (s, 2H). MS (Electrospray): m/z 223.9 (M+).

1. temperaturemixture was heated
2. temperatureto reflux conditions for two hours until no starting material
3. temperatureAfter cooling
4. customreaction to 0° C.
5. customreaction
6. customReaction
7. extractionwas extracted with ethyl acetate (3×150 ml)
8. dry with materialwere dried over MgSO4 and Na2SO4
9. filtrationAfter filtering mixture
10. concentrationthe collected filtrate was concentrated in vacuo
11. customto give a crude yellow solid

ORD-Eintrag

ord-666e5b391bbb4f03b14ba796c6bdc0c1

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07745452B2