Diethyl Ether → HCID 12297606, compound

A solution of anthranilonitrile (1 equiv., Aldrich) in diethyl ether (2.4 M) was cooled to 0° C. and treated with propylmagnesium chloride (2.5 equiv., Aldrich; 2.0 M in Et2O) in a dropwise manner over the course of an hour. After addition of 25% of the Grignard reagent, an additional {fraction (1/10)} volume of Et2O was added. The cooling bath was removed and stirring of the suspension continued for 5 hours. The reaction was returned to 0° C. and cautiously quenched with 3 N HCl. The cooling bath was removed and stirring continued for 30 minutes. The mixture was made basic by the addition of solid NaOH. The contents were extracted thrice with ethyl acetate; brine was added to help break up the suspension. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was chromatographed eluting with 95:5 hexanes/ethyl acetate.

1. customThe cooling bath was removed
2. customwas returned to 0° C.
3. customcautiously quenched with 3 N HCl
4. customThe cooling bath was removed
5. stirringstirring
6. waitcontinued for 30 minutes
7. additionThe mixture was made basic by the addition of solid NaOH
8. extractionThe contents were extracted thrice with ethyl acetate
9. additionbrine was added
10. washThe combined extracts were washed with brine
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated
14. customThe crude residue was chromatographed
15. washeluting with 95:5 hexanes/ethyl acetate

ORD record

ord-177139a8944145ac8fe26c4fd9ca664b

Source dataset

uspto-grants-2005_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06838455B2