Nitric Acid → 4-Methoxy-2-methyl-5-nitropyridine

HRID 2370879

Reaktionsgleichung

Reaktionsgleichung von HRID 2370879
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:9])[CH:4]=1.[N+:10]([O-])([OH:12])=[O:11].[OH-].[Na+]>OS(O)(=O)=O>[CH3:1][O:2][C:3]1[C:8]([N+:10]([O-:12])=[O:11])=[CH:7][N:6]=[C:5]([CH3:9])[CH:4]=1

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 47377584-Methoxy-2-methylpyridine

Produkt 1

HCID 735537124-Methoxy-2-methyl-5-nitropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a stirred solution of 4-methoxy-2-methylpyridine (25 g, 0.148 mol) in conc. H2SO4 (17 mL, S. D. Fine, India), a mixture of H2SO4 (17 mL, S.D. Fine, India) and 65% HNO3 (22 mL, Rankem, India) was added in a drop-wise fashion at 0° C. over 30 min. The resulting solution was heated at 65° C. for 12 h. After completion, the reaction mixture was poured in to ice water and neutralized (PH˜8) with 40% NaOH solution to give a yellow precipitate. The precipitate was further stirred and filtered, dried to give a mixture of 3-nitro (major product) and the desired 5-nitro isomers. The product was isolated by column chromatography, silica gel (230-400), eluting with 15% EtOAc in petroleum ether to give the title compound as yellow needles. 1H NMR (400 MHz, DMSO-d6) δ: 8.86 (s, 1H), 7.33 (s, 1H), 3.99 (s, 3H), 2.52 (s, 3H). MS (ESI, positive ion) m/z: 169.0 (M+H).

Aufarbeitung

  1. additionwas added in a drop-wise fashion at 0° C. over 30 min
  2. customto give a yellow precipitate
  3. filtrationfiltered
  4. customdried
  5. customto give
  6. additiona mixture of 3-nitro (major product)
  7. customThe product was isolated by column chromatography, silica gel (230-400)
  8. washeluting with 15% EtOAc in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-ea1ebfaff8704f94b6b69ad7f1a71c17
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710043B2

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