2. Academic Validation
  3. A convenient synthesis of 7-halo-1-indanones and 8-halo-1-tetralones

A convenient synthesis of 7-halo-1-indanones and 8-halo-1-tetralones

  • J Org Chem. 2003 Dec 26;68(26):10195-8. doi: 10.1021/jo035289s.
Phong Nguyen 1,  Evelyn Corpuz,  Todd M Heidelbaugh,  Ken Chow,  Michael E Garst
Affiliations

Affiliation

  • 1 Allergan, Inc., 2525 Dupont Drive, Irvine, California 92623, USA.
PMID: 14682726 DOI: 10.1021/jo035289s
Abstract

A regioselective oxidation of N-indan-4-yl-acetamide or N-(5,6,7,8-tetrahydronaphthalen-1-yl)acetamide with potassium permanganate followed by acidic hydrolysis gave 7-aminoindan-1-one or 8-aminotetral-1-one in good yield. The amino ketones were converted to the corresponding 7-haloindanone or the 8-halotetralone. Another method to prepare 7-haloindan-1-ones was completed by a cyclization of 3-chloro-1-(2-halophenyl)propan-1-one under Friedel-Crafts conditions to produce the product in gram quantity.

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