Ethyl 1-cyclopentyl-2-(4-nitrophenyl)benzimidazole-5-carboxylate → Ethyl 2-(4-aminophenyl)-1-cyclopentylbenzimidazole-5-carboxylate

HRID 1181323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181323
[CH:1]1([N:6]2[C:10]3[CH:11]=[CH:12][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:14][C:9]=3[N:8]=[C:7]2[C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>O1CCCC1.C(O)C.[C].[Pd]>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([C:7]2[N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:10]3[CH:11]=[CH:12][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:14][C:9]=3[N:8]=2)=[CH:21][CH:22]=1

Komponenten

5

Edukt 1

HCID 10293086Ethyl 1-cyclopentyl-2-(4-nitrophenyl)benzimidazole-5-carboxylate

Produkt 1

HCID 10132552Ethyl 2-(4-aminophenyl)-1-cyclopentylbenzimidazole-5-carboxylateAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 1-cyclopentyl-2-(4-nitrophenyl)benzimidazole-5-carboxylate (12 g) obtained in Example 21 was dissolved in tetrahydrofuran (200 ml) and ethyl alcohol (50 ml), 7.5% palladium carbon (50% wet, 1 g) was added. The mixture was hydrogenated for 1 hr at atmospheric pressure. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. Tetrahydrofuran was added to the residue to allow crystallization and the crystals were collected by filtration to give the title compound (11 g, yield 98%).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTetrahydrofuran was added to the residue
  4. customcrystallization
  5. filtrationthe crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-5c8293e940474812a326724a6c5128a5
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285551B2

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