Acetic Acid → 4-(1-methyl-1H-benzoimidazol-2-ylamino)-phenol

HRID 410186

Reaktionsgleichung

Reaktionsgleichung von HRID 410186
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:20]([CH3:21])[C:19]3[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=3[N:17]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(O)(=O)C>C1COCC1.CO.[OH-].[OH-].[Pd+2]>[CH3:21][N:20]1[C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[N:17]=[C:16]1[NH:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1

Komponenten

6

Edukt 2

HCID 176Acetic AcidHCID 59327107(4-benzyloxy-phenyl)-(1-methyl-1H-benzoimidazol-2-yl)-amine

Produkt 1

HCID 593270144-(1-methyl-1H-benzoimidazol-2-ylamino)-phenol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of compound (4-benzyloxy-phenyl)-(1-methyl-1H-benzoimidazol-2-yl)-amine (1.8 g, 5.4 mmol) in 18 mL of THF and 18 mL of MeOH was added Pd(OH)2 (0.36 g, 20%) and 9 mL of acetic acid. The resulting mixture was kept and kept at 50 psi H2 atmosphere for 3 h. The reaction mixture was then filtered over a cake of Celite™. The filtrate was concentrated and purified by silica gel column chromatography (EtOAc/hexane) to get desired product 4-(1-methyl-1H-benzoimidazol-2-ylamino)-phenol. [M+1]=240

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered over a cake of Celite™
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel column chromatography (EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b3546f7818374aefac7a71c96db7517d
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759532B2

Verknüpfte Notizen

Wird geladen…