Synthesis question

[Adamska]

So maybe this isn't on the MCAT, but this problem has been bugging me for a while:

"Outline a four-step synthesis of aniline out of cyclopentanone. You may use any other organic or inorganic reagant at your disposal."

Um...Grignard doesn't look like it could work (although I don't see why it would). Demjanov rearrangement doesn't look good either (at least not for four steps...).

1. Enamine formation: 1-cyclopentenyl-pyrrolidine

And...that's about as far as I can get atm.

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[not respect]

i dont know this might work, i just came up with it but my orgo is pretty rusty still.

1) ring expansion with diazomethane to cyclohexanone (forgot the name, but the epoxide is the minor product)
2) cyclohexanone + phthalimide -> enamine (hopefully)
3) enamine + TiCl4/Et3N -> aniline derivative
4) aniline derivative + HBr + HOAc -> aniline (amide hydrolysis)

it's pretty random, but it might work