Phenylacetonitrile to phenylethylamine Reductions
Reduction of some functional groups with zirconium tetrachloride/sodium borohydride.
Itsuno, Shinichi; Sakurai, Yoshiki; Ito, Koichi.
Synthesis (1988), (12), 995-6.
Abstract
A novel reducing agent prepd. from ZrCl4 and NaBH4 reduces various functional groups including C:O, C:N, and C.tplbond.N bonds in excellent yield (85-96%) under mild conditions.
Supported nickel-catalyzed hydrogenation of aromatic nitriles under low pressure conditions.
Takamizawa, Satoshi; Wakasa, Noriko; Fuchikami, Takamasa.
Synlett (2001), (10), 1623-1625.
Abstract
Hydrogenation of arom. nitriles takes place under the mild conditions using supported Ni catalysts to afford aminomethyl-substituted aroms. in good yields.
Convenient synthesis of protected primary amines from nitriles.
Caddick, Stephen; Haynes, Alexandra K. De K.; Judd, Duncan B.; Williams, Meredith R. V.
Tetrahedron Lett. (2000), 41(18), 3513-3516.
Abstract
Investigations into the use of nickel chloride and sodium borohydride for the redn. of nitriles showed the secondary amine dimers to be the major products under normal conditions. The addn. of a suitable trapping agent, such as di-tert.-Bu dicarbonate, allowed the isolation of the protected primary amines.
Electrocatalytic reduction of nitriles on Raney nickel.
Muthukumaran, A.; Krishnan, V.
Bull. Electrochem. (1991), 7(9), 410-11.
Abstract
An electrochem. method for the prepn. of primary amines from org. nitriles using a Raney nickel cathode is reported. It has been obsd. that it is possible to reduce benzyl cyanide to b-phenylethylamine with an yield efficiency of 85% and to reduce benzonitrile to benzylamine with an yield efficiency of 20%.
b-Phenylethylamine by electrolytic reduction of benzyl cyanide using deposited iron black cathode.
Udupa, Handady Venkatakrishna; Krishnan, Venkatasubramanian; Muthukumaran, Arunachalam.
Indian (1984), 6 pp. IN 153683 A 19840804
Abstract
In this improved process Fe black cathode deposited an a graphite substrate is used as the cathode in a diaphragm cell. The catholyte is aq. ethanolic (NH4)2SO4 contg. benzyl cyanide and the anolyte 10% H2SO4. The anode is a hollow perforated cylinder of Pb-Ag alloy and the reaction vessel is PVC. Electrolysis was carried out at 5 A/dm2 using 500 A at 10-12 V with a current efficiency of 28% and a yield of 56%. The use of Fe black cathodes decreased the cost of b-phenylethylamine considerably.
Fully Informed Jury! (http://www.fija.org/)
(http://www.fija.org/)
> Suggested search areas: nitroalkene reductions w/o LAH
> or catalytic hydrogenation under pressure
rhodium: this is exactly what i've searched already some months ago !
for those interessted in catalytic hydrogenation WITHOUT(!)
overpressure under mild conditions, i highly recomend:
"Synthesis of PEA's by Hydrogenation of b-nitrostyrenes"
Bull.Chem.Soc.Jpn., Vol.63, No.4, 1990, pp.1252-1254
Masahiko Hohno, Shigehiro Sasao and Shun-Ichi Murahashi
never fear, it's in english ! a general procedure is
describe using H2, Pd/C and HCl(aq) in EtOH. Stirring
at 0°C for 3h followed by a classical workup. they've
prepared several PEA's and their HCL-salts like:
- mescaline (yield 65%)
- 3,4-methylenedioxyPEA (yield 71%)
shulgin's alkyloxy-substituted-PEA's like IP, E, ASB are
surley also accessible by this procedure.
it won't get easier ;)
Edit: the full article has been uploaded to https://www.thevespiary.org/rhodium/Rhodium/chemistry/ns.hydrogenation.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/ns.hydrogenation.html)
/Rhodium