Nitric Acid → 4-Acetamido-2-hydroxy-5-nitrobenzoic acid

HRID 2205116

Reaktionsgleichung

Reaktionsgleichung von HRID 2205116
[N+:1]([O-:4])(O)=[O:2].[C:5]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([OH:18])[CH:10]=1)(=[O:7])[CH3:6]>C(O)(C(F)(F)F)=O>[C:5]([NH:8][C:9]1[C:17]([N+:1]([O-:4])=[O:2])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([OH:18])[CH:10]=1)(=[O:7])[CH3:6]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 655094-Acetamidosalicylic acid

Produkt 1

HCID 672874384-Acetamido-2-hydroxy-5-nitrobenzoic acidAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Nitric acid (fuming) (23.8 g, 378 mmol, 1.20 equiv) was added in portions under 50° C. to a mixture of 4-acetamido-2-hydroxybenzoic acid (61.4 g, 315 mmol, 1.00 equiv) and TFA (700 mL) in a 2-L round-bottom flask. The resulting solution was allowed to react, with stirring, for 3 hr at room temperature before being concentrated under vacuum. The residue was dissolved in 800 mL of acetone, stirred for 15 min. at reflux, then cooled. The solids were collected by filtration, giving 21.1 g (28%) of 4-acetamido-2-hydroxy-5-nitrobenzoic acid as an orange solid.

Aufarbeitung

  1. customto react
  2. concentrationbefore being concentrated under vacuum
  3. dissolutionThe residue was dissolved in 800 mL of acetone
  4. stirringstirred for 15 min.
  5. temperatureat reflux
  6. temperaturecooled
  7. filtrationThe solids were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-6eff936efc6a4aeb84ebc961e2d0f6fc
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09370522B2

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