Hydrochloric Acid → 3-(Methylamino)-4-nitrobenzoic acid

HRID 412702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412702
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1OC)([O-:3])=[O:2].[CH3:15][NH2:16].Cl>>[CH3:15][NH:16][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2])[C:8]([OH:10])=[O:9]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 787643-Methoxy-4-nitrobenzoic acid

Produkt 1

HCID 221846233-(Methylamino)-4-nitrobenzoic acidAusbeute 73 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture comprising 4-nitro-3-methoxybenzoic acid (5.0 g, 25.4 mmol) and aqueous methylamine (40%, 15 mL) is a sealed tube was heated in an oil bath at 100° C. for 12 hours, allowed to cool to room temperature, and then poured into a stirring slurry of 1M aqueous hydrochloric acid and ice to give an orange precipitate. The precipitate was collected by filtration, rinsed with water and recrystallized from hot ethanol to provide 3-methylamino-4-nitrobenzoic acid as a bright red crystalline solid (3.6 g, 73% yield); 1H-NMR (300 MHz, DMSO-d6): 13.5 (s), 8.3 (q), 8.2 (d), 7.4 (s), 7.1 (d), 3.0 (d).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customto give an orange precipitate
  3. filtrationThe precipitate was collected by filtration
  4. washrinsed with water
  5. customrecrystallized from hot ethanol

Quellen und Nachweise

ORD-Eintrag
ord-d353319eaea84c35ba97bca3607701d0
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562854B2

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