CA1066291A - 3-formyl-4-methyl-2,6-dihydroxypyridine and a process for its preparation - Google Patents
3-formyl-4-methyl-2,6-dihydroxypyridine and a process for its preparationInfo
- Publication number
- CA1066291A CA1066291A CA284,121A CA284121A CA1066291A CA 1066291 A CA1066291 A CA 1066291A CA 284121 A CA284121 A CA 284121A CA 1066291 A CA1066291 A CA 1066291A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- dihydroxypyridine
- formyl
- formula
- alkali metal
- 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
- AMAQHIAMQNRYPP-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1H-pyridine-3-carbaldehyde Chemical compound CC1=CC(O)=NC(O)=C1C=O AMAQHIAMQNRYPP-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 10
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 9
- -1 alkaline earth metal salts Chemical class 0.000 claims abstract description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000008030 elimination Effects 0.000 claims abstract description 4
- 238000003379 elimination reaction Methods 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims description 3
- RVTMFKLYYJMPGT-UHFFFAOYSA-N C(=O)C=1C(=NC(=CC1C)O)O.[K] Chemical compound C(=O)C=1C(=NC(=CC1C)O)O.[K] RVTMFKLYYJMPGT-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 150000004793 2,6-dihydroxypyridines Chemical class 0.000 abstract description 3
- 239000013067 intermediate product Substances 0.000 abstract description 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JJHVYGVVMBYCMQ-UHFFFAOYSA-N 6-hydroxy-4-methyl-1h-pyridin-2-one Chemical compound CC=1C=C(O)NC(=O)C=1 JJHVYGVVMBYCMQ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- C07D213/69—Two or more oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762635206 DE2635206A1 (de) | 1976-08-05 | 1976-08-05 | 3-formyl-4-methyl-2,6-dihydroxypyridin und ein verfahren zu seiner herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1066291A true CA1066291A (en) | 1979-11-13 |
Family
ID=5984778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA284,121A Expired CA1066291A (en) | 1976-08-05 | 1977-08-04 | 3-formyl-4-methyl-2,6-dihydroxypyridine and a process for its preparation |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5321173A (enrdf_load_stackoverflow) |
| BE (1) | BE857479A (enrdf_load_stackoverflow) |
| BR (1) | BR7705105A (enrdf_load_stackoverflow) |
| CA (1) | CA1066291A (enrdf_load_stackoverflow) |
| DE (1) | DE2635206A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2360577A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1542818A (enrdf_load_stackoverflow) |
| IT (1) | IT1143754B (enrdf_load_stackoverflow) |
| NL (1) | NL7708447A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4288440A (en) | 1980-08-29 | 1981-09-08 | The Upjohn Company | Pyridinones |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2230392A1 (de) * | 1972-06-22 | 1974-01-31 | Cassella Farbwerke Mainkur Ag | Substituierte pyridinverbindungen und verfahren zu ihrer herstellung |
-
1976
- 1976-08-05 DE DE19762635206 patent/DE2635206A1/de not_active Withdrawn
-
1977
- 1977-07-29 NL NL7708447A patent/NL7708447A/xx not_active Application Discontinuation
- 1977-08-03 BR BR7705105A patent/BR7705105A/pt unknown
- 1977-08-04 CA CA284,121A patent/CA1066291A/en not_active Expired
- 1977-08-04 GB GB3275677A patent/GB1542818A/en not_active Expired
- 1977-08-04 BE BE179909A patent/BE857479A/xx unknown
- 1977-08-04 JP JP9304477A patent/JPS5321173A/ja active Pending
- 1977-08-04 IT IT2648577A patent/IT1143754B/it active
- 1977-08-04 FR FR7724060A patent/FR2360577A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2360577A1 (fr) | 1978-03-03 |
| NL7708447A (nl) | 1978-02-07 |
| IT1143754B (it) | 1986-10-22 |
| DE2635206A1 (de) | 1978-02-09 |
| BE857479A (fr) | 1978-02-06 |
| JPS5321173A (en) | 1978-02-27 |
| BR7705105A (pt) | 1978-05-02 |
| FR2360577B1 (enrdf_load_stackoverflow) | 1979-07-20 |
| GB1542818A (en) | 1979-03-28 |
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