Li, Shuan published the artcileSynthesis of hydralazine hydrochloride with by products in manufacture of o-cyanobenzyl chloride, Related Products of nitriles-buliding-blocks, the publication is Jingxi Shiyou Huagong (2008), 25(2), 32-35, database is CAplus.
A method for the synthesis of the title compound [i.e., hydralazine hydrochloride, 1-hydrazinylphthalazine hydrochloride (1:1)] is reported here. Hydralazine hydrochloride was synthesized from the byproducts, containing o-cyanotoluene, o-cyanobenzyl chloride and o-cyanobenzal chloride with the mass percentage of 10%, 30% and 50%, resp., generated from the manufacture of o-cyanobenzyl chloride. Effects of reaction temperature and time and ratio of reactants on the yield of o-cyanobenzaldehyde and hydralazine hydrochloride were investigated. The procedures and optimized conditions were found as follows: the byproduct reacted with chlorine at 150-155° in the presence of initiator, to give o-cyanobenzal chloride with purity of above 85%. Secondly, o-cyanobenzal chloride and sodium methoxide, in molar ratio of 1:2.05, were refluxed for 20 h to produce a corresponding acetal. Thirdly, that acetal was hydrolyzed with HCl, in n(acetal):n(HCl) = 1:3.9, at 0° for 3 h to obtain o-cyanobenzaldehyde (90.5% yield). Finally, hydralazine hydrochloride was synthesized (75% yield) by refluxing o-cyanobenzaldehyde and hydrazine for 8 h at a molar ratio of 1:3.5 in the presence of HCl and methanol.
Jingxi Shiyou Huagong published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Related Products of nitriles-buliding-blocks.
Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts