GB1127042A - Synthesis of pyridoxine - Google Patents

Synthesis of pyridoxine

Info

Publication number
GB1127042A
GB1127042A GB4575065A GB4575065A GB1127042A GB 1127042 A GB1127042 A GB 1127042A GB 4575065 A GB4575065 A GB 4575065A GB 4575065 A GB4575065 A GB 4575065A GB 1127042 A GB1127042 A GB 1127042A
Authority
GB
United Kingdom
Prior art keywords
pyridoxine
oxazole
butene
hydrochloride
alkoxy
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
GB4575065A
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.)
Tanabe Seiyaku Co Ltd
Original Assignee
Tanabe Seiyaku 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 Tanabe Seiyaku Co Ltd filed Critical Tanabe Seiyaku Co Ltd
Publication of GB1127042A publication Critical patent/GB1127042A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
    • C07D263/36—One oxygen atom
    • C07D263/42—One oxygen atom attached in position 5

Landscapes

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

Abstract

1,127,042. 2 - Methyl - 3 - pyridinols; pyridoxine. TANABE SEIYAKU CO. Ltd. 28 Oct., 1965 [12 Dec., 1964; 14 June, 1965], No. 45750/65. Headings C2C and C2V. 4,5 - Disubstituted - 2 - methyl - 3 - pyridinol compounds or hydrochloride addition salts thereof of formula in which X and Y are each a hydroxymethyl, carboxyl, cyano, alkyl ester residue, alkoxy, alkanoyloxy or amino group or X and Y when taken together are a divalent group of the formula -COOCO- or -CH 2 OCH 2 - are prepared by reacting an alkyl 5-alkoxy-1,3- oxazole-4-yl-acetic acid or a salt thereof with a dienophilic compound X-CH=CH-Y in which X and Y are as defined above. Dienophilic compounds may be maleic and fumaric acid, nitriles, anhydrides and alkyl esters thereof, 1,4-dihydroxy-butene-2, 1,4-dialkoxy-butene-2, 1 ,4-dialkanoyloxy-butene-2, 1 ,4-diaminobutene-2, 2,5-dihydrofuran and 4-alkanoyloxycrotonitrile. Pyridoxine, one of the desired products is obtained directly by reaction of the oxazole with 1 ,4-dihydroxybutene-2, or by hydrolysis when alkoxymethyl or acyloxymethyl groups are substituents, or by reduction, e.g. with lithium aluminium hydride when carboxyl, alkoxycarbonyl or alkanoyloxymethyl are substituents, or by reduction and diazotization when cyano groups are substituents. Examples describe the reaction of 5-ethoxy-1,3-oxazole-4-yl -acetic acid and salts thereof, with ethyl maleate to yield diethyl - 3 - hydroxy - 2 - methyl - pyridine-4,5-dicarboxylate hydrochloride which is reduced to pyridoxine hydrochloride with lithium aluminium hydride; with fumaronitrile to yield 4,5-dicyano-3-hydroxy-2-methyl-pyridine which is reduced in the presence of Raney nickel followed by diazotization to pyridoxine hydrochloride; with 1,4-dimethoxy-butene-2 and 1,4-dihydroxy-butene-2 to yield pyridoxine prepared as hydrochloride ; with maleic anhydride to yield a product which is reduced with lithium aluminium hydride to pyridoxine hydrochloride; with 2,5-dihydrofuran to form an inner ether of pyridoxine; and with 1,4- diamino-butene-2 the product of which is diazotized to pyridoxine hydrochloride. The 5-alkoxy-1,3-oxazole-4-yl acetic acid and salts thereof are prepared by heating 8 dialkyl N- formyl aspartate in the presence of a dehydrating agent and converting the resulting alkyl 5- alkoxy - 1,3 - oxazole - 4 - yl - acetate to 5- alkoxy-1,3-oxazole-4-yl-acetic acid or salt.
GB4575065A 1964-10-31 1965-10-28 Synthesis of pyridoxine Expired GB1127042A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP6195764 1964-10-31
JP7013064 1964-12-12
JP1788565 1965-03-27
JP3566465 1965-06-14
JP4498365 1965-07-24

Publications (1)

Publication Number Publication Date
GB1127042A true GB1127042A (en) 1968-09-11

Family

ID=27519967

Family Applications (2)

Application Number Title Priority Date Filing Date
GB5755866A Expired GB1127044A (en) 1964-10-31 1965-10-28 Pyridinol compounds and a process for preparing the same
GB4575065A Expired GB1127042A (en) 1964-10-31 1965-10-28 Synthesis of pyridoxine

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB5755866A Expired GB1127044A (en) 1964-10-31 1965-10-28 Pyridinol compounds and a process for preparing the same

Country Status (7)

Country Link
BE (1) BE671385A (en)
BR (1) BR6574130D0 (en)
CH (1) CH494758A (en)
DE (1) DE1620539A1 (en)
DK (1) DK116209B (en)
GB (2) GB1127044A (en)
NL (2) NL6513977A (en)

Also Published As

Publication number Publication date
GB1127044A (en) 1968-09-11
CH494758A (en) 1970-08-15
DK116209B (en) 1969-12-22
NL130991C (en)
BR6574130D0 (en) 1973-08-16
BE671385A (en) 1966-02-14
NL6513977A (en) 1966-05-02
DE1620539A1 (en) 1970-06-04

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