Tert-butyl 4-cyanobenzoate → 4-(Amino-hydroxyimino)methylbenzoic acid t-butyl ester

HRID 376538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 376538
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:17][OH:18].C(=O)([O-])O.[Na+]>C(O)(C)(C)C.O>[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:8]=[CH:9][C:10]([CH:13]=[N:14][O:18][NH2:17])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 271408Tert-butyl 4-cyanobenzoateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 544161174-(Amino-hydroxyimino)methylbenzoic acid t-butyl esterAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a mixture of 21.2 ml of t-butanol and 2.1 ml of water were dissolved 4.3 g of 4-cyanobenzoic acid t-butyl ester, 1.84 g of hydroxylamine hydrochloride and 2.31 g of sodium hydrogencarbonate. The solution was stirred for 2 hours at 80° C. To the reaction mixture was added water, and the mixture was subjected to extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The concentrate was purified by means of a silica gel column chromatography (hexane/ethyl acetate=1/1), followed by crystallization from hexane to afford 4.41 g of the titled compound as colorless needles.

Aufarbeitung

  1. extractionthe mixture was subjected to extraction with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe concentrate was purified by means of a silica gel column chromatography (hexane/ethyl acetate=1/1)
  4. customfollowed by crystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-18d60609761c4e48b958d5aeb1d64897
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020334

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