Ammonia → 2-(6-Bromopyridin-2-yl)-2-hydroxyacetamide

HRID 1500201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500201
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:13])[C:9](OC)=[O:10])[CH:5]=[CH:4][CH:3]=1.[NH4+:14].[Cl-].N>CO>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:13])[C:9]([NH2:14])=[O:10])[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 59825086Methyl 2-(6-bromopyridin-2-yl)-2-hydroxyacetate

Produkt 1

HCID 898154332-(6-Bromopyridin-2-yl)-2-hydroxyacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-(6-bromopyridin-2-yl)-2-hydroxyacetate (0.5, g, 2.03 mmol), NH4Cl (0.1, g) and NH3, (4N in MeOH) was shaken at room temperature over night. The solvent was removed under vacuum then added water (5, mL) and CHCl3, (20, mL) The organic layer was concentrated and purified by chromatographed over silica gel with 50% EtOAc in hexanes to yield 2-(6-bromopyridin-2-yl)-2-hydroxyacetamide as a yellow solid (0.2, g, 16%). 1H NMR (600, MHz, DMSO-d6) 7.77, (1H, dd, J=7.8, & 8.4, Hz), 7.58, (1H, d, J=8.4, Hz), 7.51-7.52, (2H, m), 7.35, (1 H, s), 6.23, (1H, d, J=0.5, Hz, —OH), 4.91 (1H, d, J=0.6, Hz).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. concentrationadded water (5, mL) and CHCl3, (20, mL) The organic layer was concentrated
  3. custompurified
  4. customby chromatographed over silica gel with 50% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-eca519a3a8374bc2b3b91d67ec1a8cce
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206127B2

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