Potassium Hydroxide → 6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-amine

HRID 1042338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1042338
CC(C)(C)C([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([O:14][N:15]=[C:16]([C:23]2[N:27]([CH3:28])[N:26]=[N:25][N:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:13])[N:7]=1)=O.[OH-].[K+]>C(O)C>[CH3:28][N:27]1[C:23]([C:16](=[N:15][O:14][CH:12]([C:8]2[N:7]=[C:6]([NH2:5])[CH:11]=[CH:10][CH:9]=2)[CH3:13])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:24][N:25]=[N:26]1

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 866499712,2-dimethyl-N-{6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-yl}propanamide

Produkt 1

HCID 866499726-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-amineAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2,2-dimethyl-N-{6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-yl}propanamide (19.7 g, 48.3 mmol, 1 eq.) in 200 ml of ethanol, was added potassium hydroxide (88.4 g, 1.57 mol, 32.6 eq.). The reaction mixture was stirred and heated to reflux for 4 hrs. After evaporation of the solvent, The residue was taken up with water (300 ml) and extracted with EtOAc (100 ml). The aqueous layer was separated and extracted twice with EtOAc (100 ml). The organics were combined, dried over MgSO4 and concentrated. The crude material was purified by chromatography on silica gel to give 6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-amine (10.7 g, 90% pure, 61% yield)

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 4 hrs
  3. customAfter evaporation of the solvent
  4. extractionextracted with EtOAc (100 ml)
  5. customThe aqueous layer was separated
  6. extractionextracted twice with EtOAc (100 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe crude material was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b9009fd8fd864abc8c0e1bd9efb1f714
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557849B2

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