Ethylenediamine → HCID 59749539, compound

HRID 747275Notes

Reaction equation

HRID 747275 reaction equation
[NH2:1][CH:2]([CH:5]([C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2)[CH3:6])[C:3]#[N:4].C(N)CN>CO.[Ni]>[N:12]1[C:13]2[C:8](=[C:7]([CH:5]([CH3:6])[CH:2]([NH2:1])[CH2:3][NH2:4])[CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 59749552HCID 59749552, compound

Product 1

HCID 59749539HCID 59749539, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In a Parr bottle, a mixture of 2-amino-3-quinolin-5-yl-butyronitrile (Intermediate-E2) (5.38 g, 25.4 mmol) in MeOH (100 mL) and ethylene diamine (3.2 mL, 47.8 mmol) was reacted with Raney 2800 nickel (18.9 g) and bubbled with ammonia gas for 10 m. The Parr bottle was pressurized with hydrogen at 50 psi and shaken on a Parr apparatus for 2.5 h at rt. The mixture was filtered through celite, washed with MeOH (3×) and evaporated to leave a residue. This material was placed onto a column and eluted with a gradient of 1% to 5% sat. NH3-MeOH:CH2Cl2 to give 3-quinolin-5-yl-butane-1,2-diamine (Intermediate E3) 3.9 g (71%).

Workup

  1. custombubbled with ammonia gas for 10 m
  2. filtrationThe mixture was filtered through celite
  3. washwashed with MeOH (3×)
  4. customevaporated
  5. customto leave a residue
  6. washeluted with a gradient of 1% to 5% sat. NH3-MeOH

Sources & evidence

ORD record
ord-741e2fc219bc4327832e1183ede31bd7
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

Loading…