m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 1819463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1819463
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)(C)(C)C.[Cl:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([O:22]O)=[O:21]>CCO>[CH:13]1[CH:12]=[N+:11]([O-:21])[CH:10]=[C:9]([CH2:8][NH2:7])[CH:14]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([OH:22])=[O:21]

Komponenten

5

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 13948280tert-Butyl (pyridin-3-ylmethyl)carbamate

Produkt 2

HCID 4473-Chlorobenzoic AcidHCID 2985103-Aminomethylpyridine-N-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To pyridin-3-ylmethyl-carbamic acid tert-butyl ester (3.89 g, 18.7 mmol) dissolved in EtOH (50 mL), was added 3-chloroperoxybenzoic acid (4.7 g, 27.4 mmol). After 4 hours the volatiles were removed in vacuo and the crude was redissolved in CH2Cl2 (25 mL). To this solution was added TFA (25 mL) and the reaction was stirred at 25° C. for 2 h then the volatiles were removed in vacuo. The crude was redissolved in CH2Cl2 and evaporated. This procedure was done twice more. (1-Oxy-pyridin-3-yl)-methylamine was obtained with contamination of 3-chlorobenzoic acid, but carried further without any additional purification (2.74 g).

Aufarbeitung

  1. customAfter 4 hours the volatiles were removed in vacuo
  2. dissolutionthe crude was redissolved in CH2Cl2 (25 mL)
  3. additionTo this solution was added TFA (25 mL)
  4. customthe volatiles were removed in vacuo
  5. dissolutionThe crude was redissolved in CH2Cl2
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-aeff01c2c8bf433d8d1819f7576bf421
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601714B2

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