HCID 59691669, compound → HCID 59691619, compound

HRID 898528Notes

Reaction equation

HRID 898528 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[CH:5]=[CH:6][C:7]=1[C:8]#[C:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13]>[Ni].CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15]

Participants

4

Reactant 1

HCID 59691669HCID 59691669, compound

Product 1

HCID 59691619HCID 59691619, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

2.00 g (7.498 mmol) of 3-chloro-4-(3-diethylamino-prop-1-ynyl)-phenylamine (intermediate product Z13b) was added to a suspension of 0.50 g Raney-Ni in 50 mL abs. MeOH and the mixture was hydrogenated for 2.5 hours at RT and 50 psi H2 atmosphere. The catalyst was filtered off, the filtrate evaporated down i. vac. and the residue was purified by column chromatography (silica gel, gradient dichloromethane/10% conc. aqueous ammonia in MeOH 100:0→5:95).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated down i
  3. customand the residue was purified by column chromatography (silica gel, gradient dichloromethane/10% conc. aqueous ammonia in MeOH 100:0→5:95)

Sources & evidence

ORD record
ord-ab591cb1ae63498681986d1d9604fcb0
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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