GB862581A - Improvements in or relating to the preparation of 3-pyridinols - Google Patents
Improvements in or relating to the preparation of 3-pyridinolsInfo
- Publication number
- GB862581A GB862581A GB21257A GB21257A GB862581A GB 862581 A GB862581 A GB 862581A GB 21257 A GB21257 A GB 21257A GB 21257 A GB21257 A GB 21257A GB 862581 A GB862581 A GB 862581A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- oxidation
- pyridinol
- amino group
- acid
- 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
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
- C07D213/62—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
- C07D213/62—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
- C07D213/67—2-Methyl-3-hydroxy-4,5-bis(hydroxy-methyl)pyridine, i.e. pyridoxine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
3-Pyridinols of the formula: <FORM:0862581/IV (b)/1> (wherein Z is hydrogen or CH2OH and R2 and R4 are hydrogen or alkyl) are prepared by oxidizing substituted furans of the formula: <FORM:0862581/IV (b)/2> (wherein Y is hydrogen or CH2OR1, R1 being hydrogen or aryl, and R5 is an amino group or a protected amino group) or acid-addition salts thereof by a halogen in water or by other chemical oxidizing agents in water or an aqueous or anhydrous alcohol ROH (wherein R is an alkyl, hydroxyalkyl or cycloalkyl group of not more than 6 carbon atoms) and hydrolysing to produce the required 3-pyridinol. Suitable oxidizing agents include oxyhalogenic and hypohalogenous acids and their salts, hydrogen peroxide, inorganic peroxy acids and salts thereof, organic peracids, dichromates and chromic acid, permanganates, nitric acid and nitrogen oxides. The oxidation product formed is directly hydrolysed to the 3-pyridinol, and the oxidation and hydrolysis are desirably effected at a pH of between zero and 10, the pH being adjusted if necessary by addition of an organic or mineral acid, preferably hydrochloric acid. An oxidation catalyst, such as ferrous sulphate or vanadium pentoxide, may also be added. Protection of the amino group in the starting material may be effected by conversion to the corresponding acyl, carbamate or N-mono- or N-di-carbamoyl derivative, but the amino group, and the CH2OH groups when present, are preferably free. Numerous examples describe the preparation of 3-pyridinol ,2-methyl-3-pyridinol and pyridoxine by the process of the invention using a variety of oxidizing agents, and a further example describes the oxidation of 2-(a -aminoethyl)-3:4-bis-(hydroxymethyl)-furan to 2-(a -aminoethyl)-3:4-bis-(hydroxymethyl) - 2:5- dimethoxy-and-diethoxy-2:5-dihydrofurans using aqueous sodium hypochlorite and hydrochloric acid in methanol and ethanol respectively, without a subsequent hydrolysis. The Provisional Specification refers to the use of anhydrous alcohols, aqueous alcohols, water and other solvents in general as reaction media in the oxidation process, and provides two further examples illustrating the oxidizing action of chlorine in aqueous methanol.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21257A GB862581A (en) | 1957-01-02 | 1957-01-02 | Improvements in or relating to the preparation of 3-pyridinols |
| CH5208457A CH367169A (en) | 1953-11-30 | 1957-10-29 | Process for the preparation of 3-pyridinols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21257A GB862581A (en) | 1957-01-02 | 1957-01-02 | Improvements in or relating to the preparation of 3-pyridinols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB862581A true GB862581A (en) | 1961-03-15 |
Family
ID=9700386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21257A Expired GB862581A (en) | 1953-11-30 | 1957-01-02 | Improvements in or relating to the preparation of 3-pyridinols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB862581A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4192946A (en) * | 1978-06-29 | 1980-03-11 | Ciba-Geigy Corporation | Process for producing 3-hydroxy-5-halopyridines |
| EP0939079A1 (en) * | 1998-02-27 | 1999-09-01 | Novartis AG | Process for the preparation of substituted pyridines |
-
1957
- 1957-01-02 GB GB21257A patent/GB862581A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4192946A (en) * | 1978-06-29 | 1980-03-11 | Ciba-Geigy Corporation | Process for producing 3-hydroxy-5-halopyridines |
| EP0939079A1 (en) * | 1998-02-27 | 1999-09-01 | Novartis AG | Process for the preparation of substituted pyridines |
| US6133447A (en) * | 1998-02-27 | 2000-10-17 | Novartis Crop Protection, Inc. | Process for the preparation of substituted pyridines |
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