Ammonium Hydroxide → 2-Amino-6-chloronicotinic acid

HRID 30096

Reaktionsgleichung

Reaktionsgleichung von HRID 30096
Cl[C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[NH4+:13]>>[NH2:13][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

3

Edukt 2

HCID 14923Ammonium HydroxideHCID 8540472,6-Dichloronicotinic acid

Produkt 1

HCID 122639922-Amino-6-chloronicotinic acidAusbeute 34 %

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

A solution of 2,6-dichloronicotinic acid (10 g, 46.9 mmol, Aldrich 90%) was dissolved in concentrated ammonium hydroxide (100 mL, 29.4%, Fisher) and heated at 130-160° C. in a pressure bottle for 1-2 days before solvent was removed in vacuo. The residue was treated with water and the pH was lowered to ˜8 with concentrated hydrochloric acid. The resulting mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried, concentrated and the crude product was recrystallized from ethyl acetate to give 2-Amino-6-chloro-nicotinic acid as white crystalline (2.74g, 34 % yield). HRMS, observed: 172.0042, Calcd for M+: 172.0040

Aufarbeitung

  1. customwas removed in vacuo
  2. additionThe residue was treated with water
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customthe crude product was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6237c299266048aca0b33d6d74d4643e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423051B2

Verknüpfte Notizen

Wird geladen…