Hydrochloric Acid → HCID 90011309, Verbindung

HRID 1054912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054912
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[C:7]([N+:13]([O-])=O)=[N:8][C:9]([Br:12])=[CH:10][CH:11]=1.Cl.C(=O)(O)[O-].[Na+]>CO.[Fe]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[C:7]([NH2:13])=[N:8][C:9]([Br:12])=[CH:10][CH:11]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 90011186(6-Bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester

Produkt 1

HCID 90011309HCID 90011309, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(6-Bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester (10.9 g, 37.5 mmol) was dissolved in methanol (90 mL). Concentrated HCl (10 mL) was then added followed by iron (6.4 g, 110 mmol). The reaction mixture was stirred at 60° C. for 1 hour. Then, the reaction mixture was cooled to room temperature and neutralized with solid sodium bicarbonate. The insoluble iron salts were removed by centrifugation. Silica gel was then added to the supernatant and the solvents were removed under reduced pressure. The resulting crude material was purified by column chromatography (SiO2, EtOAc/hexanes) to give (2-amino-6-bromopyridin-3-yloxy)acetic acid methyl ester. Yield 4.0 g (15 mmol, 40%). LCMS (ESI): calc. C8H9BrN2O3=260, 262; obs. M+H=261, 263.

Aufarbeitung

  1. customThe insoluble iron salts were removed by centrifugation
  2. additionSilica gel was then added to the supernatant
  3. customthe solvents were removed under reduced pressure
  4. customThe resulting crude material was purified by column chromatography (SiO2, EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-5e0bf88fb9bb48c591a353ace90aeff0
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394315B2

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