Water → 2-Amino-3-nitrobenzamide

HRID 736696

Reaktionsgleichung

Reaktionsgleichung von HRID 736696
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)(Cl)=O.[OH-].[NH4+:19].O>C(COC)OC>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:19])=[O:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 2196332-Amino-3-nitrobenzoic acid

Produkt 1

HCID 107974762-Amino-3-nitrobenzamideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 2-amino-3-nitrobenzoic acid (prepared using the procedure as described in U.S. Pat. No. 6,737,421, EXAMPLE 2, part b) in dimethoxyethane (DME, 7.1 mL/g), was added thionyl chloride (1.33 equivalents). The mixture was stirred at 50° C. for 12 hours, cooled and slowly added to concentrated ammonium hydroxide (22 equivalents). The mixture was stirred at 50° C. for 2 hours, water was added, and the mixture was cooled and filtered. The solid was washed with water and isopropanol, and dried under vacuum to give the title compound (89% yield).

Aufarbeitung

  1. temperaturecooled
  2. stirringThe mixture was stirred at 50° C. for 2 hours
  3. temperaturethe mixture was cooled
  4. filtrationfiltered
  5. washThe solid was washed with water and isopropanol
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-10723559ed7945fd884e11a711969e85
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595406B2

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