Friedel—Crafts Synthesis of 4-(3,4-Dichlorophenyl)-3,4-Dihydro-1(2H)- Naphthalenone, A Key Intermediate in The Preparation of The Antidepressant Sertraline

Journal of Organic Chemistry

Volumn 55, Issue 16, 1990, Pages 4971-4973

  Quallich, George J ^a   Friedmann, Robert C ^a   Williams, Michael T ^b  

^a PFIZER INC   (United States)

^b Research Network   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

SERTRALINE;

ARTICLE; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

EID: 0025180785     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00303a046     Document Type: Article

References (16)

1. Koe, B. K.; Weissman, A.; Welch, W. M.; Browne, R. G. J. Exp. Ther. 1983, 226. 686.
2. Reinher, F. W.; Byerley, W. F.; Ward, M. F.; Lebegue, B. J.; Wender, P. H. Psychopharmacol. Bull. 1988. 24. 200.
3. U.S. Patent 4,536,518.
4. Welch, W. M.; Kraska, A. R.; Sarges, R.: Koe, B. K. J. Med. Chem. 1984. 27. 1508–1515.
5. Streck, E. A.; Brundage, R. P.; Fletcher, L. T. J. Am. Chem. Soc. 1953, 75, 1117–1119.
6. Barton, D. H. R.; Ollis, W. D. Comprehensive Organic Chemistry; Pergamon Press: New York. 1979: Vol. 1. p. 277.
7. U.S. Patent 4,777, 288;
8. Chem. Abstr. 1989,110, 57312.
9. Truce, W. E.; Olson, C. E. J. Am. Chem. Soc. 1952, 74. 4721.
10. Brown, H. C.; Grayson, M. J. Am. Chem. Soc. 1953, 75, 6285–6292.
11. After 5 days at 70 °C, 80% conversion to the tetralone 5 occurred with the remainder of the material being diaryl acid 4. Gore, P. H.; Hoskins, J. A. J. Chem. Soc. 1964, 5666.
12. U.S. Patent 4,839, 104.
13. Chem. Abstr. 1990, 112, 55242.
14. Wawzonek, S.; Kozikowski, J. J. Am. Chem. Soc. 1954, 76,1641.
15. Sindelar, K.; Svatek, E.; Kakac, B., Hradil, F.; Protiva, M. Collect. Czech. Chem. Commun. 1972, 37, 1195–1205.
16. Merck index, Tenth Edition, 4703.