7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile → 5-Aminomethyl-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one

HRID 2427717

Reaktionsgleichung

Reaktionsgleichung von HRID 2427717
[CH3:1][C:2]1[CH:3]=[C:4]([C:24]#[N:25])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2>C1COCC1.C(O)C.[Ni].O.[NH4+].[OH-]>[NH2:25][CH2:24][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([CH3:1])[CH:3]=1)[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:21])[F:22])=[CH:15][CH:14]=1)[CH2:7]2

Komponenten

7

Edukt 1

HCID 579493637-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile

Produkt 1

HCID 579493205-Aminomethyl-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 14923Ammonium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 7-methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile (0.104 g, 0.3 mmol) in THF (1 mL) and ethanol (4 mL) was treated with a suspension of Raney nickel in water (1 mL) and aqueous NH4OH (0.5 mL). The mixture was stirred at ambient temperature for 12 h under hydrogen atmosphere (1 atm.). After this time GC-MS indicated that all the starting material was consumed. The reaction mixture was filtered and concentrated to afford the desired product. The material was used without purification.

Aufarbeitung

  1. customwas consumed
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d9e73f0acdaf49be8303457ad70748c1
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968570B2

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