GB1199737A - Process for the preparation of 3-Hydroxyisoxazole Compounds and Alkali Metal Salts thereof - Google Patents

Process for the preparation of 3-Hydroxyisoxazole Compounds and Alkali Metal Salts thereof

Info

Publication number
GB1199737A
GB1199737A GB3808767A GB3808767A GB1199737A GB 1199737 A GB1199737 A GB 1199737A GB 3808767 A GB3808767 A GB 3808767A GB 3808767 A GB3808767 A GB 3808767A GB 1199737 A GB1199737 A GB 1199737A
Authority
GB
United Kingdom
Prior art keywords
alkali metal
phenyl
hydroxyisoxazoles
formula
per mol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB3808767A
Inventor
Kazuo Tomita
Mitsuo Nagano
Hidehiko Oka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sankyo Co Ltd
Original Assignee
Sankyo Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sankyo Co Ltd filed Critical Sankyo Co Ltd
Priority to GB3808767A priority Critical patent/GB1199737A/en
Publication of GB1199737A publication Critical patent/GB1199737A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/12—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1,199,737. 3-Hydroxyisoxazoles. SANKYO CO. Ltd. 18 Aug., 1967, No. 38087/67. Heading C2C. 3-Hydroxyisoxazoles of the formula wherein R represents hydrogen or an alkyl, phenyl, substituted phenyl, carboxyl or dialkoxymethyl group having 1-5 carbon atoms in each alkoxy moiety, and the alkali metal salts thereof, are prepared by reacting hydroxylamine, or an acid addition salt thereof, with either a compound of the formula where R<SP>11</SP> is hydrogen, or an alkyl, phenyl, substituted phenyl, alkoxycarboxyl, the alkoxy moiety containing 1-3 carbon atoms, or dialkoxy methyl group, R<SP>1</SP> is a C 1-5 alkyl group, and X is halogen, or a compound of the formula where Y and Z are different and represent hydrogen or halogen, in the presence of an alkali metal hydroxide to form the alkali metal salt of the hydroxyisoxazole and, if desired, treating the salt with an organic or inorganic acid to liberate the free hydroxy compound, the alkali metal hydroxide being used in an amount of at least 3 mols. per mol. of dihalo reactant or at least 2 mols. per mol. of olefinic reactant. The reaction is preferably effected at 30-120‹ C. in an inert solvent using 1-1À5 mol. hydroxylamine per mol. dihalo or olefinic reactant. Examples relate to the preparation of 5-methyl, 5-isopropyl, 5-phenyl, 5-(4-rnethylphenyl), 5-(4- chlorophenyl), 5-(4<SP>1</SP>-biphenylyl), 5-(4-methoxyphenyl), 5-(4-nitrophenyl), 5-diethoxymethyl, 5-ethyl, 5-isobutyl, 5-n-decyl, 5-n-propyl, 5- carboxy-, 5-(4-cyanophenyl), 5-(3-nitrophenyl) and 5-(2-methoxyphenyl)-3-hydroxyisoxazoles.
GB3808767A 1967-08-18 1967-08-18 Process for the preparation of 3-Hydroxyisoxazole Compounds and Alkali Metal Salts thereof Expired GB1199737A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3808767A GB1199737A (en) 1967-08-18 1967-08-18 Process for the preparation of 3-Hydroxyisoxazole Compounds and Alkali Metal Salts thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3808767A GB1199737A (en) 1967-08-18 1967-08-18 Process for the preparation of 3-Hydroxyisoxazole Compounds and Alkali Metal Salts thereof

Publications (1)

Publication Number Publication Date
GB1199737A true GB1199737A (en) 1970-07-22

Family

ID=10401084

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3808767A Expired GB1199737A (en) 1967-08-18 1967-08-18 Process for the preparation of 3-Hydroxyisoxazole Compounds and Alkali Metal Salts thereof

Country Status (1)

Country Link
GB (1) GB1199737A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5472972A (en) * 1992-05-07 1995-12-05 Sankyo Company, Limited Agrochemical compositions and methods employing hymexazol and 1,2-benzisothiazolin-3-one
CN104529925A (en) * 2014-12-19 2015-04-22 武汉工程大学 5-(4-nitrophenyl)-3-hydroxylisoxazole and preparation process and use thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5472972A (en) * 1992-05-07 1995-12-05 Sankyo Company, Limited Agrochemical compositions and methods employing hymexazol and 1,2-benzisothiazolin-3-one
US5554391A (en) * 1992-05-07 1996-09-10 Sankyo Company, Limited Composition containing the dihydrate of the calcium salt of 3-hydroxy-5-methylisoxazole and cupric hydroxide
CN104529925A (en) * 2014-12-19 2015-04-22 武汉工程大学 5-(4-nitrophenyl)-3-hydroxylisoxazole and preparation process and use thereof

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee