Someone of you beez asked of this ref.
Synthesis of 3-substituted phenylethylamines by catalitic reduction of nitrostyrenes.
Synthesis of starting aldehydes [8, 9, 10] was carried out by known methods, namely introduction in a molecule of vanillin I- or Br-atom, with the subsequent replacement of halogen on - oxy- or alkoxy groups. The appropriate styrenes [11, 12] were obtained by condensation of aldehydes with nitromethane with the catalytic additives of methylamine. The carrying out of condensation at the presence of ammonium acetate in acetic acid instead of methylamine greatly reduced yield or yielded slowly decomposed products.
3-methoxy-4,5-dioxyphenylethylamine
A suspension of 3 g 3-methoxy-4,5-dioxynitrostyren in 80 mls of acetic acid with simultaneous feeding of Hydrogenium is added to 3 g of vigorously shaken palladium black in 65 mls of glacial acetic acid and 2 mls of concentrated sulfuric acid previously sated with Hydrogenium for 30 minutes. After end of absorbtion of calculated amount of Hydrogenium the catalyst was separated, acetic acid was distilled off in vacuum; the stayed oil was cooled to the beginning of crystallization. The deposit was filtered off and washed on the filter with 15 mls of acetone. Yield 2 g (51,5 %), m. p. 107-108 deg. C.(from water).
then they make freebase and hydrocloride.
freebase m. p. 173-174 deg. C.(from alcohol)
hydrocloride m. p. 198-199 deg. C.(from alcohol)
Similarly 3,5-dimethoxy-4-oxyfhenylethylamine and 3-methoxy-4-oxy-5-bromfhenylethylamine were obtained.
3,5-dimethoxy-4-oxyfhenylethylamine
freebase m. p. 153-154 deg. C.(from alcohol)
bisulpfate m. p. 143-144 deg. C(from dry alcohol)
hydrocloride m. p. 256-257 deg. C.(from alcohol and ether 1:2)
Yield 54.4 of bisulpfate
3-methoxy-4-oxy-5-bromfhenylethylamine
freebase m. p. 169-170 deg. C.(from m-xylene)
bisulpfate m. p. 217-218 deg. C(from alcohol)
hydrocloride m. p. 176-177 deg. C.(from alcohol and ether 1:2)
Yield 49.8 of bisulpfate
Refs:
I ask those who have access to this articles to post them here.
[11] Ð. Smith. J. Chem. Soc., 1958, 3740
[12] J. Pepper, J.MacDonald. Canad. J. Chem. 31, 476(1953)
[8] F. Benington, R. Morin, L. Clarc, J. Org. Chem., 20, 1292(1955)
[9] F. Benington, R. Morin, L. Clarc, J. Am. Chem. Soc.,76. 5555(1954)
[10] is a Russian journal and I'll try to find it soon.