Water → N-(2-Methoxy-6-nitrophenyl)valeroamide

HRID 653713

Reaktionsgleichung

Reaktionsgleichung von HRID 653713
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:4]=1[NH2:5].S(=O)(=O)(O)O.[OH2:18].[OH-].[Na+]>C(OC(=O)CCCC)(=O)CCCC>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:4]=1[NH:5][C:6](=[O:18])[CH2:4][CH2:3][CH2:9][CH3:8]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 854916-Nitro-o-anisidine

Produkt 1

HCID 19792196N-(2-Methoxy-6-nitrophenyl)valeroamideAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 74959Valeric anhydrideLösungsmittel

Versuchsvorschrift

To a mixture of 2-methoxy-6-nitroaniline (5.9 g) in valeric anhydride (14 g) was added a catalytic amount of conc. sulfuric acid, which was stirred for 1.5 hour at 130°-140° C. To the reaction mixture was added water, which was made basic with 6N NaOH. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and dried. The solvent was distilled off. The residue was purified by column chromatography on silica gel. Crude crystals thus obtained were recrystallized from ethyl acetate-hexane to give colorless crystals (3.2 g, 36%), m.p. 113°-114° C.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. distillationThe solvent was distilled off
  5. customThe residue was purified by column chromatography on silica gel
  6. customCrude crystals thus obtained
  7. customwere recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-c0fd67846f7542e49c8920a16b2d71e3
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05128356

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