A new route for manufacture of 3-cyano-1-naphthalenecarboxylic acid

Organic Process Research and Development

Volumn 7, Issue 1, 2003, Pages 74-81

  Ashworth, I W ^a,b   Bowden, M C ^a,b   Dembofsky, B ^a   Levin, D ^a   Moss, W ^a   Robinson, E ^a,b   Szczur, N ^a,b   Virica, J ^a,b  

^a ASTRAZENECA   (United Kingdom)

^b JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 BROMOCOUMALATE; 3 CYANO 1 NAPHTHALENECARBOXYLIC ACID; 4 BROMO 2 NAPHTHOATE; ACID; BENZENE DERIVATIVE; BROMINE DERIVATIVE; CARBON; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER; NAPHTHALENE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; COST; DIELS ALDER REACTION; PROCESS DEVELOPMENT; SCALE UP; SYNTHESIS;

EID: 0037283277     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op025571l     Document Type: Article

References (21)

1. Bernstein, P. R.; Dedinas, R. F.: Russell, K.; Shenvi, A. PCT Patent WO 0002859, 2000.
2. Rumsey, W. L.; Aharony, D.; Bialecki, R. A.; Abbott, B. M.; Barthlow, H. G.; Caccese, R.; Ghanekar, S.; Lengel, D.; McCarthy. M.; Wenrich, B.; Undem, B.; Ohnmacht, C.; Shenvi, A.; Albert, A. S.; Brown, F.; Bernstein, P. R.; Russell, K. J. Pharmacol. Exp. Ther. 2001, 298, 307.
3. Bernstein, P. R. Aharony, D.; Albert, J. S.; Andisik, D.; Barthlow, H. G.; Bialecki, R.; Davenport, T.; Dedinas, R. F.; Dembofsky, B. T.; Koether, G.; Kosmider, B. J.; Kirkland, K.; Ohnmacht, C. J.; Potts, W.; Rumsey, W. L.; Shen, L.; Shenvi, A.; Sherwood, S.; Stollman, D.; Russell, K. Bioorg. Med. Chem. Lett. 2001. 11, 2769.
4. Donaldson, N. The Chemistry and Technology of Naphthalene Compounds; Edward Arnold: London, 1958; p 373.
5. Donaldson, N. The Chemistry and Technology of Naphthalene Compounds; Edward Arnold: London, 1958; p 445.
6. Dewar, M. J. S.; Grisdale, P. J. J. Am. Chem. Soc. 1962, 84, 3541.
7. Whitmore, F. C.; Fox. A. L. J. Am. Chem. Soc. 1929, 51, 3363.
8. Escudero, S.; Pérez, D.; Guitián, E.; Castedo, L. Tetrahedron Lett. 1997, 38, 5375.
9. Wiley, R. H.; Smith, N. R. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. 4, p 201.
10. von-Pechmann, H. Annalen 1891, 264, 261.
11. Dare, D. L.; Entwistle, I. D.; Johnstone, R. A. W. J. Chem. Soc., Perkin Trans. I 1973, 1130.
12. Wiley, R. H.; Knabeschuh, L. H. J. Am. Chem. Soc. 1955, 77, 1615.
13. Tsai, L.; Silverton, J. V.; Lingh, H. T. J. Org. Chem. 1978, 43, 4417.
14. Kvita, V.; Sauter, H. Helv. Chim. Acta 1990, 73, 883.
15. Atanes, N.; Castedo, L.; Guitián. E.; Saá, C.; Saá, J. M.; Suau, R. J. Org. Chem. 1991, 56, 2984.
16. Stephenson, E. F. M.; Organic Syntheses; John Wiley & Sons: New York. 1955; Collect. Vol. 3, p 475.
17. Logullo, F. M.; Scitz, A. H.; Friedman, L. Organic Syntheses; John Wiley & Sons: New York, 1973; Collect. Vol. 5, p 54.
18. Mutaszak, C. A. Chem. Eng. News 1971, 49, 39.
19. Moseley, J. D.: Moss. W. O.; Welham, M. J.; Ancell, C. L.; Banister, J.; Bowden, S. A.; Norton, G.; Young. M. J. Org. Process Res. Dev. 2003, 7, 58-66.
20. Bailey, T. D. U.S. Patent 4,230,864, 1980
21. Marko, I. E.; Evans, G. R. Tetrahedron Lett. 1993, 34, 7309.