One of you beez asked for this reference:
Synthesis of 3-substituted phenylethylamines by catalytic reduction of nitrostyrenes
Synthesis of the starting aldehydes [8,9,10] was carried out by known methods, namely halogenation of vanillin with either iodine or bromine, with the subsequent replacement of the halogen with either a hydroxy or an alkoxy group. The appropriate styrenes [11,12] were obtained by condensation of the aldehydes with nitromethane using methylamine as catalyst. Carrying out the condensation in the presence of ammonium acetate in acetic acid instead of methylamine greatly reduced yield or gave unstable products, which slowly decomposed.
3-methoxy-4,5-dihydroxy-phenylethylamine
With simultaneous introduction of hydrogen gas, a suspension of 3g 3-methoxy-4,5-dihydroxynitrostyrene in 80 mls of acetic acid was added to 3g of vigorously shaken palladium black in 65 mls of glacial acetic acid and 2 mls of concentrated sulfuric acid previously saturated with hydrogen gas for 30 minutes. After the calculated amount of hydrogen had been absorbed, the catalyst was filtered off, the acetic acid was distilled off in vacuum; and the remaining oil was cooled to induce crystallization. The precipitate was filtered off and washed on the filter with 15 mls of acetone. Yield 2g (51.5%), mp 107-108°C (from water).
Then they go on to make the amine freebase and hydrochloride salt.
Freebase mp. 173-174°C. (from alcohol)
Hydrochloride mp. 198-199°C. (from alcohol)
Similarly 3,5-dimethoxy-4-hydroxyphenylethylamine and 3-methoxy-4-hydroxy-5-bromo-phenylethylamine were obtained.
3,5-Dimethoxy-4-hydroxyphenylethylamine
Freebase mp. 153-154°C. (from alcohol)
Bisulfate mp. 143-144°C (from dry alcohol)
Hydrochloride mp. 256-257°C (from alcohol/ether 1:2)
Yield 54.4% of bisulfate.
3-Methoxy-4-hydroxy-5-bromophenylethylamine
Freebase mp. 169-170°C (from m-xylene)
Bisulfate mp. 217-218°C (from alcohol)
Hydrochloride mp. 176-177°C (from alcohol/ether 1:2)
Yield 49.8% of bisulfate.
References:
I ask those who have access to these articles to post them here:
[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] A Russian journal I'll try to find soon.
[11] Ð. Smith. J. Chem. Soc., 1958, 3740
[12] J. Pepper, J.MacDonald. Can. J. Chem. 31, 476 (1953)
http://www.chemlover.narod.ru/articles/article17.djv (http://www.chemlover.narod.ru/articles/article17.djv)
in russian. later i'll translate it.