Ammonium formate → 4-[2-(Oxan-2-yloxy)ethoxy]aniline

HRID 450512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 450512
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>CCO.[Pd]>[O:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]1[O:13][CH2:12][CH2:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 108908362-[2-(4-Nitrophenoxy)ethoxy]oxane2×

Produkt 1

HCID 110209174-[2-(Oxan-2-yloxy)ethoxy]aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 2-({2-[(4-nitrophenyl)oxy]ethyl}oxy)tetrahydro-2H-pyran (Intermediate 17) (1.33 g, 5 mmol) in EtOH (50 mL) was added Pd/C (catalytic amount) and ammonium formiate (0.9 g, 10 eq). The reaction was stirred to 40° C. for 2 hours. After filtration on celite, the solvent was evaporated and the residue was poured in water, extracted with ether and dried over sodium sulphate and evaporated. The title compound was obtained as a dark oil (0.8 g, 68%). LC/MS: m/z 238 (M+H)+, Rt: 2.38 min.

Aufarbeitung

  1. filtrationAfter filtration on celite
  2. customthe solvent was evaporated
  3. additionthe residue was poured in water
  4. extractionextracted with ether
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-deae8ce8f9d345edadeae3956c2458e5
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486977B2

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