Nitric Acid → 2-Chloro-5-methoxy-3-methyl-4-nitropyridine 1-oxide

HRID 69315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69315
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([O:13][CH3:14])=[CH:8][N+:7]=1[O-:15].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[Cl:5][C:6]1[C:11]([CH3:12])=[C:10]([N+:1]([O-:4])=[O:2])[C:9]([O:13][CH3:14])=[CH:8][N+:7]=1[O-:15]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 867178152-Chloro-5-methoxy-3-methylpyridine 1-oxide

Produkt 1

HCID 867178162-Chloro-5-methoxy-3-methyl-4-nitropyridine 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Concentrated nitric acid (2.5 mL) was added drop-wise to a 0° C. solution of C2 (350 mg, 2.02 mmol) in concentrated sulfuric acid (2.5 mL). The reaction mixture was heated at 90° C. for 1 hour, then cooled to room temperature and poured onto crushed ice. The resulting mixture was neutralized to pH 6-7 with saturated aqueous sodium carbonate solution, and extracted with ethyl acetate. The combined organic layers were washed with water, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo to provide the product as a light yellow solid. Yield: 370 mg, 1.69 mmol, 84%. LCMS m/z 219.0, 221.1 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 8.65 (s, 1H), 3.94 (s, 3H), 2.31 (s, 3H).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. additionpoured
  3. customonto crushed ice
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. washwashed with saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-638a42ae056845ba92bf5d870e224a00
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822494B2

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