Ammonia → HCID 53755479, compound

HRID 910713Notes

Reaction equation

HRID 910713 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][CH2:16][C:17]#[N:18])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[NH4+].[OH-].N>CCO.[Ni]>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[CH2:15][CH2:16][CH2:17][NH2:18])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 14923Ammonium HydroxideHCID 14069397HCID 14069397, compound

Product 1

HCID 53755479HCID 53755479, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-anthracen-9-yl-propionitrile (3.0 g, 13 mmol) in EtOH (140 mL) was added concentrated NH4OH (14 mL) and Raney nickel (14 g), and ammonia gas was bubbled through the mixture at 0° C. for 10 minutes. The suspension was hydrogenated at room temperature for 24 hours. Air was bubbled through the solution and Raney nickel was removed by filtration. The filtrate was concentrated, and the oily residue was dissolved in CH2Cl2, washed with an aqueous solution of Na2CO3 (10%), dried over MgSO4 and concentrated to give 3-anthracen-9-yl-propylamine as a brown oil (2.60 g, 85% yield). 1H NMR (CDCl3) δ 8.35 (1H, s), 8.30 (2H, d), 8.02 (2H, d), 7.54-7.46 (4H, m), 3.68 (2H, t), 2.95 (2H, t), 2.01-1.95 (2H, m) 1.32 (2H, br-s).

Workup

  1. customwas bubbled through the mixture at 0° C. for 10 minutes
  2. customAir was bubbled through the solution and Raney nickel
  3. customwas removed by filtration
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe oily residue was dissolved in CH2Cl2
  6. washwashed with an aqueous solution of Na2CO3 (10%)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-938be2b682de4e5fa487f4754f1bde87
Source dataset
uspto-grants-2011_09
Patent number
US08022214B2

Reaction notes

Loading…