Ammonia → (3,4-Dimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-methylamine

HRID 1610045Notes

Reaction equation

HRID 1610045 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:6]2[CH:7]([C:9]#[N:10])[CH2:8][C:5]=2[CH:4]=1.N>[Ni].CO>[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:6]2[CH:7]([CH2:9][NH2:10])[CH2:8][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 2905443,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

Product 1

HCID 423512(3,4-Dimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-methylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Introduce 4,5-dimethoxy-1-cyano-benzocyclobutane (6 kg), methanol (30 liters), Raney nickel (0.6 liters) and ammonia (7.32 kg) into a hydrogenator. After having purged with nitrogen and then with hydrogen, hydrogenate at 60° C. and at 30 bar until the theoretical amount of hydrogen has been absorbed. After returning to 20° C., filter off the catalyst, rinsing it with methanol, and then evaporate off the solvent. The title compound is obtained in the form of an oil, in a quantitative yield.

Workup

  1. customAfter having purged with nitrogen
  2. customwith hydrogen, hydrogenate at 60° C. and at 30 bar until the theoretical amount of hydrogen has been absorbed
  3. customAfter returning to 20° C.
  4. filtrationfilter off the catalyst
  5. washrinsing it with methanol
  6. customevaporate off the solvent

Sources & evidence

ORD record
ord-81c874d1c78a4007903f142a7348f84d
Source dataset
uspto-grants-2006_01
Patent number
US06982350B2

Reaction notes

Loading…