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 2427717Notes

Reaction equation

HRID 2427717 reaction equation
[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

Participants

7

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 5

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14923Ammonium HydroxideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-d9e73f0acdaf49be8303457ad70748c1
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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