Ammonia → HCID 22147746, compound

HRID 1824309Notes

Reaction equation

HRID 1824309 reaction equation
C([CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])#N.[NH3:13]>C(O)C.[Ni]>[NH2:13][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 2736747(2-Methoxyphenoxy)acetonitrile

Product 1

HCID 22147746HCID 22147746, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of the 2-cyanomethoxyanisole (5.6 g, 0.034 mol) in anhydrous ammonia (25 ml) and ethanol (50 ml) was heated to 120° C. at 500 psi for 12 h in the presence of raney nickel (1.4 g). The reaction mixture was filtered, concentrated under reduced pressure, the residue taken up in ether, and washed with 1.2 M HCl. The acidic phase was then rendered basic (pH=12) with careful addition of solid KOH and the alkaline solution extracted with ether. The organic phase was dried (MgSO4) and concentrated under reduced pressure to give the product (1.99 g, 35%) as an oil. IR. NMR. MS.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. washwashed with 1.2 M HCl
  4. additionwith careful addition of solid KOH
  5. extractionthe alkaline solution extracted with ether
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-976374cd924e41e29fb2109e8a8d5f74
Source dataset
uspto-grants-2006_05
Patent number
US07041684B2

Reaction notes

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