Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1998-01-20
1999-05-25
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568735, 568634, 568440, 568328, 568303, C07C 3938, C07C 3914, C07C 4100, C07C 4752
Patent
active
059070692
ABSTRACT:
In producing nabumetone or precursor thereof, use is made of 2-bromo-6-methoxynaphthalene formed by (a) methylating 6-bromo-2-naphthol with methyl bromide or methyl chloride, in a halogen-free liquid solvent comprising at least about 40% by weight of one or more compounds of the formula RZ where R is a hydrogen atom or an alkyl group, and Z is a hydroxyl group or a cyanide group with the proviso that if Z is a cyanide group, R is an alkyl group, and in the presence of at least one strong base; and (b) recovering and purifying 2-bromo-6-methoxynaphthalene so formed. The 6-bromo-2-naphthol in turn is preferably formed by reacting 1,6-dibromo-2-naphthol with hydrogen in a halogen-containing liquid solvent comprising at least about 50% by weight of (A) at least one liquid organic halide solvent in which the halogen content has an atomic number of 35 or less or (B) a mixture of water and at least one such liquid organic halide solvent, and in the presence of catalytic amounts of (i) a tungsten carbide-based catalyst, and (ii) at least one phase transfer catalyst, most preferably while purging HBr from the reaction mixture as it is formed. In this way, the quantities of by-products formed in the overall operation are reduced, the need for use of excess iron and/or dimethyl sulfate as reaction components is avoided, and the overall efficiency of plant operation is improved especially when conducted on a large scale.
REFERENCES:
patent: 2025032 (1935-12-01), Arnold et al.
patent: 3880932 (1975-04-01), Anderson et al.
patent: 4061779 (1977-12-01), Lake et al.
patent: 4182912 (1980-01-01), Foley
patent: 4221741 (1980-09-01), Gaster
patent: 4246164 (1981-01-01), Felder et al.
patent: 4246193 (1981-01-01), Holton
patent: 4247709 (1981-01-01), Rose et al.
patent: 4270004 (1981-05-01), Rose et al.
patent: 4299844 (1981-11-01), Goudie
patent: 4420639 (1983-12-01), Lake et al.
patent: 4426392 (1984-01-01), Goudie
patent: 4515811 (1985-05-01), Holton
patent: 4556738 (1985-12-01), Kawashima et al.
patent: 4628123 (1986-12-01), Borsotti
patent: 4697036 (1987-09-01), Giordano et al.
patent: 4734507 (1988-03-01), Giordano et al.
patent: 4952596 (1990-08-01), Della Bella et al.
patent: 4988416 (1991-01-01), Troupel et al.
patent: 5093011 (1992-03-01), Friedman et al.
patent: 5132466 (1992-07-01), Dales et al.
patent: 5225603 (1993-07-01), Aslam et al.
patent: 5243088 (1993-09-01), Jacquot et al.
patent: 5256829 (1993-10-01), Jacquot
patent: 5426243 (1995-06-01), Lecouve
Summers et al., "Hydroxamic Acid Inhibitors of 5-Lipoxygenase", J. Med. Chem., 1987, vol. 30, pp. 574-580.
Wong et al., "Synthesis of Novel-centrosymmetric Crystalline Materials for Quadratic Non-linear Optics", J.Chem. Soc., Chem. Commun., 1994, pp. 249-250.
CAPLUS abstract of DE 2338811 (copy of original text enclosed).
WPIDS abstract of DE 2338811 (copy of original text enclosed).
5-Bromo-2,3-benzotropone and its Maleic Anhydride Adduct, Bull. of the Chem. Soc. of Japan, 1971, vol. 44(12) pp. 3480-3481, Ebine, et al.
4-(6-Methoxy-2-naphthyl)butan-2-one and related Analogues, a Novel Structural Class of Antiinflammatory Compounds, J. of Medicinal Chemistry, 1978, vol. 21(12), pp. 1260-1264, Goudie, et al.
3,4-Benzotropolone and Related Compounds. VI. Brominated 6-Hydroxy-2,3-benzotropone (or Brominated 3-Hyroxy-4,5-benzotropone). Formation and Reaction, Bull of the Chem. Soc. of Japan, 1968, vol. 41, pp. 2949-2953, Hoshino, et al.
Hard Acid and Soft Nucleophile Systems. 8. Reductive Dehalogenation of o- and p-Halophenols and Their Derivatives, J. Org. Chem., 1984, vol. 49, pp. 3641-3643, Node, et al.
Reversible Bromination. I. Isomerization and Disproportionation of p-Bromophenols, The J. of Org. Chem., 1970, vol. 35(1), pp. 16-19, O'Bara, et al.
X-Philic Reactions, Chem. Rev., 1982, vol. 82(6), pp. 615-624, Zefirov, et al.
Aslam, et al., "Convenient Synthesis of Nabumetone", Synthesis, Nov. 1989, vol. 11, pp. 869-870.
Chatterjea, et al., "Condensation of Mannich Base Salts with Phenols: Orientation of Adducts", Indian Journal of Chem., vol. 11, Mar. 1973, pp. 214-218.
Chen, et al., "Synthesis of Nabumetone by Palladium Catalyzed Coupling", Zhong Guo Yi Yao Gong Ye Za Zhi, vol. 25 (2), 1994, translated pp. 49-50, 57.
Chen, et al., "Novel Synthesis of Nabumetone", Zhong Guo Yi Yao Gong Ye Za Zhi, 1989, vol. 20(4), translated pp. 145-146.
Horeau et al., "No. 287. Setroids Devoid of C Nucleus (III). On a Lactone Corresponding to an Isomer of Bis-Dehydroestrolactone", Soc. Chim., 5th Series, 1959--Reports, translated pp. 1854-1857.
Liu, et al., "Synthesis of Nabumetone", Yi Yao Gong Ye, 1985, vol. 16(4), translated pp. 147-149.
Yin, et al., "Experiments on Preparation of Nabumetone", Zhong Guo Yi Yao Gong Ye Za Zhi, 1990, vol. 21(5), translated pp. 195-196.
Zhang, et al., "Synthesis of a Nonsteroidal Anti-Inflammatory Agent--Nabumetone", Journal of Shenyang College of Pharmacy, vol. 5(4), Oct. 1988, Sum 37, translated pp. 259-263, 267.
Becnel Brian F.
Sabahi Mahmood
Theriot Kevin J.
Albemarle Corporation
Dees Jos,e G.
Pryor Alton
Spielman, Jr. E. E.
LandOfFree
Production of nabumetone or precursors thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Production of nabumetone or precursors thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Production of nabumetone or precursors thereof will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-401931