Water → Methyl 4-acetamido-3-hydroxybenzoate

HRID 270124

Reaktionsgleichung

Reaktionsgleichung von HRID 270124
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O)[C:5]([O:7][CH3:8])=[O:6].[H][H].O.[C:18](OC(=O)C)(=[O:20])[CH3:19]>C1COCC1.[Pd]>[C:18]([NH:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[OH:1])(=[O:20])[CH3:19]

Komponenten

7

Edukt 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 294866Methyl 3-hydroxy-4-nitrobenzoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22627408Methyl 4-acetamido-3-hydroxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A solution of methyl 3-hydroxy-4-nitrobenzoate (0.78 g, 3.96 mmol) in THF (40 ml) with Pd on charcoal (10%, 0.15 g) was stirred in the atmosphere of hydrogen at atmospheric pressure overnight. The mixture was filtered through celite. The solvent was removed in vacuo. The residue was taken into water (20 ml), and acetic anhydride (0.5 ml, 5.29 mmol) was added. The mixture was vigorously stirred at 65° C. for 30 min. After cooling to room temperature, the precipitate was collected by filtration, washed with water, and dried. White powder (0.64 g, 77%).

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. customThe solvent was removed in vacuo
  3. additionwas added
  4. temperatureAfter cooling to room temperature
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d16811778448467883d1efc1d438fa79
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449475B2

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