Can modifying the Gabriel synthesis, which is generally restricted to synthesis of primary amines, be used to synthesise secondary amines?

I have attached my idea regarding the synthesis (the final product obtained is a phthalic acid):

synthesis pathway

  • 4
    $\begingroup$ You cannot do the 2nd reaction using alcohol as solvent. It will react with the acyl chlorides/cyanides to give the diester $\endgroup$
    – Waylander
    Jul 30, 2020 at 6:51
  • 3
    $\begingroup$ Some of these intermediates feel too unstable... Is there precedent for adding HCl across an acyl cyanide twice? Practically, reductive amination is probably a simpler way of getting to secondary amines. $\endgroup$ Jul 30, 2020 at 7:18
  • 3
    $\begingroup$ The benzocyclicamide (just before adding $\ce{Mg(OH)2}$), is not stable. $\ce{HCl}$ would leave quickly, giving cyclic carboxyimine product. $\endgroup$ Jul 30, 2020 at 7:20
  • $\begingroup$ W-K reduction does not work for formamides. This looks like a lot of trouble to go to when reductive methylation procedures are well precedented, work very quickly and in high yield. $\endgroup$
    – Waylander
    Jul 30, 2020 at 7:36
  • 1
    $\begingroup$ DMSO reacts with acid chlorides $\endgroup$
    – Waylander
    Jul 30, 2020 at 8:34


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