Hydrochloric Acid → 3-Amino-5-phenylpicolinic acid

To a solution of 3-nitro-5-phenylpicolinonitrile (1 eq) in 10 mL of DMF was added tin (II) chloride dehydrate (7.0 eq) at room temperature. The reaction mixture was stirred at that temperature overnight. The mixture was diluted with 150 mL of ethyl acetate and 30 mL of triethyl amine. After filtration, the filtrate was concentrated under reduced pressure to give a solid, which was added 2 mL of concentrated HCl. The mixture was stirred in microwave at 90° C. for 10 minutes. After standing over night, the solid was collected by filtration, which was dissolved in 10 mL of 1N NaOH. The resulting mixture was extracted with 50 mL of ethyl acetate. The aqueous layer was acidified by 1 N HCl to pH 7.0 to yield 3-amino-5-phenylpicolinic acid, which was collected by filtration. LC/MS (m/z): 215.1 (MH+).

1. filtrationAfter filtration
2. concentrationthe filtrate was concentrated under reduced pressure
3. customto give a solid, which
4. stirringThe mixture was stirred in microwave at 90° C. for 10 minutes
5. waitAfter standing over night
6. filtrationthe solid was collected by filtration, which
7. dissolutionwas dissolved in 10 mL of 1N NaOH
8. extractionThe resulting mixture was extracted with 50 mL of ethyl acetate

ORD-Eintrag

ord-636abf1bf85942ff961bf0acc5cc0bc6

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08822497B2