Ammonium Hydroxide → HCID 42951958, compound

HRID 1094634Notes

Reaction equation

HRID 1094634 reaction equation
O/[N:2]=[C:3](/[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)\[CH3:4].[OH-].[NH4+]>[Ni].CO>[NH2:2][CH:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)[CH3:4]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 87086032HCID 87086032, compound

Product 1

HCID 42951958HCID 42951958, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a MeOH (30 ml) solution of 5-[(1E)-N-hydroxyethanimidoyl]-1,3-dihydro-2H-indol-2-one (0.5 g, 2.6 mmol; WO 2004108133), Raney Nickel and aqueous solution of ammonium hydroxide (10 ml) were added and the mixture was stirred for 9 hours under hydrogen (4.0 kgf/cm2). Then, the reaction was filtered off and the filtrate was evaporated to give 5-(1-aminoethyl)-1,3-dihydro-2H-indol-2-one as a free form. Then, the amine was treated with MeOH solution of 10% of chloride and recrystallized from MeOH/diethyl ether to give the title compound as a white solid. MS (ESI) m/z 177 (M+H)+

Workup

  1. filtrationThen, the reaction was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-6a153ff27e054df29f85dd291358f006
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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