Synthesis of 2,3-dihydroindole

[Sharka]

Can anybody help me with synthesis of 2,3-dihydroindole from 2-nitrotoluene. I need make it up in about seven steps.

This is my solution, but I´m not sure about the last step.

Thanks

[Horza2002]

The final step can be done, but you need to add some other reagents in there. What is the inital product when an amine reacts with a carbonyl?

 

Additionally, there is a possible alteration of your method that will get you from the 2-amino toluene (number 2) all the way to your benzyl alcohol (number 5) in a single step. Think about the position you are trying to oxidise and what reagents are out there to do this transformation (HINT: its a p-block element based reagent)

[hypervalent_iodine]

Additionally, there is a possible alteration of your method that will get you from the 2-amino toluene (number 2) all the way to your benzyl alcohol (number 5) in a single step. Think about the position you are trying to oxidise and what reagents are out there to do this transformation (HINT: its a p-block element based reagent)

 

What benzyl alcohol?

[Sharka]

The product when amine reacts with carbonyl is imine. I have to reduce it with NaBH₄ and AcOH?