January 15, 2025, 10:45:52 AM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1]   Go Down

Topic: Organic Synthesis, Problem 2  (Read 4027 times)

0 Members and 1 Guest are viewing this topic.

Offline Carcul

  • Regular Member
  • ***
  • Posts: 11
  • Mole Snacks: +0/-0
Organic Synthesis, Problem 2
« on: April 14, 2007, 05:29:49 AM »
Show how you would carry out the following conversion:

aniline  --->  2,3-dimethylindole.

(Source: adapted from an Heterocyclic Chemistry examination, September 2001, University of Coimbra)

Carcul
Logged

Offline Dolphinsiu

  • Full Member
  • ****
  • Posts: 349
  • Mole Snacks: +3/-7
  • Gender: Male
Re: Organic Synthesis, Problem 2
« Reply #1 on: April 16, 2007, 06:38:02 AM »
I guess to use 2,3-dimethyl but-2-ene to react with!
Logged

Offline AWK

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 7976
  • Mole Snacks: +555/-93
  • Gender: Male
Re: Organic Synthesis, Problem 2
« Reply #2 on: April 16, 2007, 08:14:57 AM »
what about using 2-butanone
Logged
AWK

Offline AWK

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 7976
  • Mole Snacks: +555/-93
  • Gender: Male
Re: Organic Synthesis, Problem 2
« Reply #3 on: April 16, 2007, 08:17:48 AM »
What about using 2-butanone.
None - Fisher indole synthesis need phenylhydrazine instead of aniline, but converision of aniline to that compound is easy
Logged
AWK

Offline Carcul

  • Regular Member
  • ***
  • Posts: 11
  • Mole Snacks: +0/-0
Re: Organic Synthesis, Problem 2
« Reply #4 on: April 16, 2007, 07:47:14 PM »
That's right. First let's diazotize aniline with NaNO2 in HCl at ~0ºC. Next reduce the diazonium ion to phenylhydrazine. Then reaction with butanone completes the synthesis.
Logged
Pages: [1]   Go Up
« previous next »
Sponsored Links