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

HRID 2170535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2170535
[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-381e90b114034db6a55c7486c9cdb8d4
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051281B2

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