Methanol → Methyl 2-hydroxy-5-nitronicotinate

HRID 2117170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2117170
[OH:1][C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:18]O>>[N+:11]([C:8]1[CH:7]=[C:3]([C:4]([O:6][CH3:18])=[O:5])[C:2](=[O:1])[NH:10][CH:9]=1)([O-:13])=[O:12]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178524577HCID 178524577, Verbindung

Produkt 1

HCID 7204882Methyl 2-hydroxy-5-nitronicotinateAusbeute 99 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-hydroxy-5-nitronicotinic acid (0.80 g, 4.35 mmol, Combi-Blocks) in methanol (10 mL) at 0° C. was added thionyl chloride (1 mL) dropwise. The mixture was stirred at 0° C. for 1 h, then at 60° C. for 2 h. The excess methanol was removed under reduced pressure and the residue was neutralized with aqueous sodium bicarbonate solution. The solid was collected, washed with water and dried to afford the title compound (0.85 g, 99%). 1H NMR (DMSO-d6) δ 8.44 (s, 1H), 8.34 (s, 1H), 3.67 (s, 3H); MS(ESI+) m/z 199 (M+H)+.

Aufarbeitung

  1. waitat 60° C. for 2 h
  2. customThe excess methanol was removed under reduced pressure
  3. customThe solid was collected
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-25f8f7c4238a4d0b922ed4d2f959a8a1
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439246B2

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