5
$\begingroup$

Decide major product for given reaction of electrophilic aromatic substitution:

Nitration of benz[cd]indol-2(1H)-one (CAS 130‐00‐7)

Is the major product a because of steric hindrance, or is it b because of hydrogen bonding?

$\endgroup$

1 Answer 1

5
$\begingroup$

According to this patent here, N-ethyl 1,8-naphtholactam nitrates in the 4 position i.e. structure a. It seems entirely likely the N-unsubstituted material will do likewise.

$\endgroup$
4
  • 1
    $\begingroup$ I Got the answer but I didn't understood "It seems entirely likely the N-unsubstituted material will do likewise." Meaning $\endgroup$
    – Jay
    Apr 24, 2021 at 12:49
  • 1
    $\begingroup$ Meaning I cannot find a reference to the nitration of 1,8-naphtholactam so I've quoted the nearest example. In my opinion 1,8-naphtholactam will also nitrate in the same position. $\endgroup$
    – Waylander
    Apr 24, 2021 at 12:51
  • 1
    $\begingroup$ @Waylander Is iprdb.com a reliable source from your experience? Don't you think a conventional link to Google Patents (which they seem to copy content from without any quality control) would be better? $\endgroup$
    – andselisk
    Apr 24, 2021 at 12:54
  • $\begingroup$ The reference is what Google found for me. It references the US patent so in this case it seems reliable. The result is in accord with my expectations $\endgroup$
    – Waylander
    Apr 24, 2021 at 13:10

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.