Nitrite → Methyl 3-iodo-4-methyl-5-nitrobenzoate

HRID 922446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 922446
N[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].N([O-])=O.[I-:19].[K+]>Cl.O>[I:19][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6]

Komponenten

6

Edukt 3

HCID 946NitriteHCID 4875Potassium IodideHCID 839285Methyl 3-amino-4-methyl-5-nitrobenzoate

Produkt 1

HCID 24728110Methyl 3-iodo-4-methyl-5-nitrobenzoateAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel3×

Versuchsvorschrift

To a suspension of methyl 3-amino-4-methyl-5-nitrobenzoate (36.0 g) in 6-normal hydrochloric acid (276 mL) was added dropwise a solution nitrite (13.0 g) in water (35 mL) under ice-salt-cooling over 20 minutes, and the mixture was stirred under ice-cooling for 1 hour. Then, thereto was added dropwise a solution of potassium iodide (34.1 g) in water (280 mL) under ice-cooling over 20 minutes, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added water under ice-cooling, and the mixture was extracted with chloroform. The organic layer was sequentially washed with aqueous saturated sodium thiosulfate solution and saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=50/1) to give methyl 3-iodo-4-methyl-5-nitrobenzoate [REx(14-1)] (40.5 g) as a yellow powder.

Aufarbeitung

  1. temperaturecooling over 20 minutes
  2. temperaturecooling for 1 hour
  3. temperaturecooling over 20 minutes
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. temperaturecooling
  6. extractionthe mixture was extracted with chloroform
  7. washThe organic layer was sequentially washed with aqueous saturated sodium thiosulfate solution and saturated saline
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-bf67ea49179a409a801b37d5c4714ad3
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278944B2

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