Products of o-aminobenzaldehyde thermal treatment with acetone and further with sulfuric acid [closed]








**Closed.** This question is [off-topic](/help/closed-questions). It is not currently accepting answers.
 
 






---








 **Homework questions** must demonstrate some effort to understand the underlying concepts. For help asking a good homework question, see: [How do I ask homework questions on Chemistry Stack Exchange?](https://chemistry.meta.stackexchange.com/questions/141/how-do-i-ask-homework-questions-on-chemistry-stack-exchange)




Closed 3 years ago.








[Improve this question](/posts/133445/edit) 




> 
> *o*-Aminobenzaldehyde is heated along with acetone in dilute $\ce{NaOH}$ solution to produce the major organic product (**A**), which on treatment with a catalytic amount of $\ce{H2SO4},$ produces another major organic product (**B**) formed via intramolecular reaction.
> 
> 
> What will be the products **A** and **B** formed in this reaction?
> 
> 
> 


I have tried solving it and I think **A** will be *o*-aminobenzoic acid. But I want to ask that what happens when *o*-aminobenzoic acid is reacted with catalytic amount of $\ce{H2SO4}?$




This is an example of the Friedländer synthesis of quinolines [Wikipedia article here](https://en.wikipedia.org/wiki/Friedl%C3%A4nder_synthesis).


Under catalysis by hydroxide acetone undergoes an aldol condensation with the aldehyde group to give **3**, which is your compound **A** ($\ce{R2=Me, R3=H}$). Under the catalysis of sulfuric acid **A** loses water to give the quinoline **7** (for your **B** $\ce{R2 = Me, R3=H}$).


Several reviews of the Friedländer exist, this is a good one [Chem. rev. here](https://pubs.acs.org/doi/10.1021/cr800482c). 


[![Friedländer Reaction](https://i.stack.imgur.com/9EnnV.png)](https://i.stack.imgur.com/9EnnV.png)


Image is from [ref 1](https://en.wikipedia.org/wiki/Friedl%C3%A4nder_synthesis).


 8