Preparation of a-methoxyiminocarboxylic acid methylamides and in

Details Preparation of a-methoxyiminocarboxylic acid methylamides and in Preparation of a-methoxyiminocarboxylic acid methylamides and in

1996-12-10

1999-01-05

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560 51, 560 53, 560 60, 562440, 562450, 562459, 562470, 562874, 564124, 564134, 564149, 544106, 544224, 544242, 546192, 546249, 548202, 548214, 548235, 548247, 548255, 5482672, 5483355, 5483751, 548566, 549 74, 549 80, 549491, 558371, C07C 5986, C07C 6973, C07C23106, C07C22936, C07C24908, C07C25124

Patent

active

058565604

ABSTRACT:
A process and intermediates for preparing .alpha.-methoxyiminocarboxylic acid methylamides (I) by Pinner reaction of a cyanoketone (II) with an alcohol and subsequent reaction of the resulting ester (IV) with hydroxylamine to give the oxime (V), methylation of (V) to give the oxime ether (VI) and subsequent reaction of (VI) with methylamine: ##STR1##

REFERENCES:
patent: 5194662 (1993-03-01), Brand et al.
patent: 5221762 (1993-06-01), Wingert et al.
patent: 5358968 (1994-10-01), Oberdorf et al.
patent: 5393920 (1995-02-01), Benoit et al.
patent: 5530156 (1996-06-01), Benoit et al.
Hackh's Chemical Dictionary, Fourth Ed., McGraw-Hill Book Company (1969) pp. 249 and 424.
Dehydration of 1-o-Tolyl-2.2 . . . , Roger et al.
Friedel-Crafts-Type . . . Ohwada et al., J.am. Chem. Soc. 1991, 113, 1364-1373.
Chem. Abst., vol. 100, 1984, p. 5671.
Chem. Abst., vol. 96, 1982, p. 6335.
Chem. Abst., vol. 115, 1991, p. 964.
Chem. Abst. vol. 67, 1967, p. 6012.
A New Synthetic Method of Alkyl . . . , Shimizu et al., Bull Chem. Soc. Jpn., 58, 2519-2522.
Chem. Abst 92-265140/32.
Chem. Abst 93-285392/36.
Chem. Abst 93-348301/44.
Chadwick et al., Organic Chemistry, Part 2, p. 49 (George Allen & Unwin Ltd., London), 1971.
Howard et al., "Vinylogous Urethanes in Alkaloid Synthesis: Formal Synthesis of Elaeocarpus Alkaloids," Tetrahedron Letters, vol. 21, pp. 1373-1374, 1980.
Zagar et al., "The Paterno-Buchi Reaction of Achiral and Chiral Acyl Cyanides with Furan," Chem. Ber., vol. 124, pp. 967-969, 1991.
H.C. Martin, "Orthobenzoyl-Benzoyl Chloride," J. Am. Chem. Soc., vol. 38, pp. 1142-1144, 1916.
Rees et al., "Antimalarial Activities of Some 3,5-Diamino-as-triazine Derivatives," J. Med. Chem., vol. 15, No. 8, pp. 859-861, 1972.
Pearce et al., "Rearrangements of Azidoquinones, XV. Thermal Rearrangement of 2,3-Diazido-1,4-quinones to 2-Aza-3-cyano-1,4-quinones," J. Am. Chem. Soc., vol. 97, pp. 6181-6186, 1975.
Yagupol'skii et al., "Reaction of o-Phenylenediacetic Acid with Phosphorus Pentachloride," J. Org. Chem. USSR (Engl. Transl.), vol. 11, No. 12, pp. 2580-2584, 1975.
Griffin et al., "Synthesis and Photorearrangement of Substituted K-Region Arene Oxides," Tetrahedron Lett., No. 16, pp. 1239-1242, 1976.
Achmatowicz et al., "Chemia Cajanku Karbonylu. X. . . . ", Roczniki Chemii, vol. 35, pp. 813-819, 1961.
Connors et al., "Acyl cyanides as carbonyl heterodienophiles: application to the synthesis of naphthols, isoquinolones and isocoumarins," Can. J. Chem., vol. 74, pp. 221-226, 1996.
Roger et al., "The Dehydration of 1-o-Tolyl-2.2-Diphenyl Ethylene Glycol," Rec. Trav. Chim. Pays-Bas, vol. 56, pp. 202-207, 1937.
Philip J. Kocienski, "A Directed Aldol Approach to (+)-Milbemycin Beta-sub3," J. Chem. Soc. Perkin Trans., vol. 1, pp. 2171-2181, 1987.
Itoh et al., "Synthesis of Aryl Glyxolate. I. The Reaction of Alkyl Dichloro(alkoxy)acetates with Aromatics in the Presence of Lewis Acid," Bull. Chem. Soc. Jpn., vol. 57, No. 3, pp. 810-814, 1984.
M.L. Bouveault, "Sur les acides glyoxyliques de la serie aromatique," Bull. Soc. Chim. Fr., vol. 17, pp. 363-366, 1897.
Chuit et al., "Preparation de l'aldehyde p-isopropylphenyl-acetique et de quelques-uns de ses isomers et homologues," Bull. Soc. Chim. Fr., vol. 35, pp. 200-205, 1924.

Affiliated with

Also associated with

Rating

Preparation of a-methoxyiminocarboxylic acid methylamides and in does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Preparation of a-methoxyiminocarboxylic acid methylamides and in, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation of a-methoxyiminocarboxylic acid methylamides and in will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-864255