Ammonium Chloride → 2-Ethoxy-4-aminobenzoic acid

HRID 2105829

Reaktionsgleichung

Reaktionsgleichung von HRID 2105829
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:13][C:11]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:3][CH2:1][CH3:2])[CH:12]=1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 27363472-Ethoxy-4-nitrobenzoic acid

Produkt 1

HCID 101763852-Ethoxy-4-aminobenzoic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Iron (16.19 g, 290 mmol) was added to a slurry mixture of 2-ethoxy-4-nitrobenzoic acid (24.00 g, 114 mmol) in ethanol (200 mL) and saturated aqueous solution of ammonium chloride (120 mL). The mixture was stirred at 80° C. for 2 h. The reaction mixture was cooled to room temperature and filtered through Celite. It was rinsed with methylene chloride and the combined filtrate diluted with water and extracted with methylene chloride and dried over anhydrous sodium sulfate. Evaporation of the solvent and chromatography of the brown residue over silica gel using 1-5% methanol in methylene chloride produced 4-amino-2-ethoxybenzoic acid as a yellow solid (14.94 g, 73%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. washIt was rinsed with methylene chloride
  4. additionthe combined filtrate diluted with water
  5. extractionextracted with methylene chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEvaporation of the solvent and chromatography of the brown residue over silica gel using 1-5% methanol in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-3ef8c165b34f44ce9fc441bdc116fc09
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579368B2

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