N-[4-(4-nitrophenoxy)-2-pyridinyl]-1-pyrrolidinecarboxamide → 4-(4-Aminophenoxy)-2-[(pyrrolidin-1-yl)carbonylamino]pyridine

HRID 2066261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2066261
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1

Komponenten

4

Edukt 1

HCID 57677470N-[4-(4-nitrophenoxy)-2-pyridinyl]-1-pyrrolidinecarboxamide

Produkt 1

HCID 231532634-(4-Aminophenoxy)-2-[(pyrrolidin-1-yl)carbonylamino]pyridineAusbeute 105,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Pyrrolidine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide (116.8 mg) was dissolved in tetrahydrofuran (3 ml), 20% palladium hydroxide on carbon (25.0 mg) was added under a nitrogen atmosphere at room temperature while stirring, followed by stirring under a hydrogen atmosphere for 7 hr. The atmosphere in the reaction vessel was replaced with nitrogen, and the catalyst was removed by filtration and washed with tetrahydrofuran. The solvent was removed under reduced pressure to provide the titled compound as a pale yellow solid (112 mg).

Aufarbeitung

  1. stirringby stirring under a hydrogen atmosphere for 7 hr
  2. customthe catalyst was removed by filtration
  3. washwashed with tetrahydrofuran
  4. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f6f2ca489f7348499ff63476397f2cba
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288538B2

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