Hydrogen Bromide → HCID 131731313, Verbindung

HRID 2178647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2178647
C[O:2][C:3]1[N:8]=[C:7]([C:9]([O:11]C)=[O:10])[CH:6]=[CH:5][C:4]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1.[BrH:19]>C(O)(=O)C>[BrH:19].[CH3:18][C:16]1[N:15]=[CH:14][N:13]([C:4]2[C:3](=[O:2])[NH:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=2)[CH:17]=1

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 67798582Methyl 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carboxylate

Produkt 1

HCID 131731313HCID 131731313, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of methyl 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carboxylate (C2) (3.82 g, 15.9 mmol) in acetic acid (30 mL) and aqueous hydrobromic acid (48%, 30 mL) was heated at reflux for 4 hours. The reaction was allowed to cool to room temperature, then chilled in an ice bath; the resulting precipitate was collected via filtration and washed with ice water (30 mL). Recrystallization from ethanol (20 mL) provided the title compound as a light yellow solid. Yield: 3.79 g, 12.6 mmol, 79%. LCMS m/z 220.1 (M+1). 1H-NMR (400 MHz, DMSO-d6) δ 2.34 (br s, 3H), 7.09 (d, J=7.4 Hz, 1H), 7.88-7.91 (m, 1H), 8.07 (d, J=7.6 Hz, 1H), 9.58-9.60 (m, 1H), 12.6 (v br s, 1H).

Aufarbeitung

  1. temperatureat reflux for 4 hours
  2. temperaturechilled in an ice bath
  3. filtrationthe resulting precipitate was collected via filtration
  4. washwashed with ice water (30 mL)
  5. customRecrystallization from ethanol (20 mL)

Quellen und Nachweise

ORD-Eintrag
ord-fc5cb33a2f5143a3b1ffecda01316cf2
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067934B2

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