Procaine: spot the conditions flaw

Single question

Two-step route to procaine: reduce 4-nitrobenzoic acid to PABA, then esterify with 2-(diethylamino)ethanol. The reaction classes and intermediates look right. Check the conditions on the ester-forming step.

Esterification with bifunctional amino alcohols

Chemoselectivity of acid chloride formation

Aniline protection in coupling chemistry

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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