CH640875A5 - Process for preparing pyridone dyes - Google Patents
Process for preparing pyridone dyes Download PDFInfo
- Publication number
- CH640875A5 CH640875A5 CH1251778A CH1251778A CH640875A5 CH 640875 A5 CH640875 A5 CH 640875A5 CH 1251778 A CH1251778 A CH 1251778A CH 1251778 A CH1251778 A CH 1251778A CH 640875 A5 CH640875 A5 CH 640875A5
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- carbon atoms
- hydrogen
- formula
- optionally substituted
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 20
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 carbamoylmethyl Chemical group 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- KOOMFXGDLMRWSN-UHFFFAOYSA-N n-phenylnitrous amide Chemical class O=NNC1=CC=CC=C1 KOOMFXGDLMRWSN-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 1
- SSUQTDZQLZTGGS-UHFFFAOYSA-N 2-hydroxy-6-oxo-1h-pyridine-4-carboxamide Chemical compound NC(=O)C1=CC(O)=NC(O)=C1 SSUQTDZQLZTGGS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- IMCUNHRQWWRKAQ-UHFFFAOYSA-N ethyl 1-methyl-2h-pyridine-4-carboxylate Chemical compound CCOC(=O)C1=CCN(C)C=C1 IMCUNHRQWWRKAQ-UHFFFAOYSA-N 0.000 description 1
- HJZKGSNCIHVALE-UHFFFAOYSA-N ethyl 2-hydroxy-6-oxo-1h-pyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC(O)=NC(O)=C1 HJZKGSNCIHVALE-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- NXGXIYVHHGPIBJ-UHFFFAOYSA-N n,n-diethyl-2-hydroxy-6-oxo-1h-pyridine-4-carboxamide Chemical compound CCN(CC)C(=O)C1=CC(O)=NC(O)=C1 NXGXIYVHHGPIBJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B55/00—Azomethine dyes
- C09B55/009—Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22730/78A GB1599627A (en) | 1978-05-25 | 1978-05-25 | Bleachable dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH640875A5 true CH640875A5 (en) | 1984-01-31 |
Family
ID=10184189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1251778A CH640875A5 (en) | 1978-05-25 | 1978-12-07 | Process for preparing pyridone dyes |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS54153830A (it) |
| BE (1) | BE872201R (it) |
| CH (1) | CH640875A5 (it) |
| DE (1) | DE2853354A1 (it) |
| FR (1) | FR2426717A2 (it) |
| GB (1) | GB1599627A (it) |
| IT (1) | IT1158155B (it) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3929698A1 (de) * | 1989-09-07 | 1991-03-14 | Basf Ag | Triazolopyridinfarbstoffe sowie ein verfahren zum thermischen transfer von methinfarbstoffen |
| US5162290A (en) * | 1990-04-27 | 1992-11-10 | Dai Nippon Insatsu Kabushiki Kaisha | Heat transfer sheet |
| ES2101090T3 (es) * | 1991-05-03 | 1997-07-01 | Basf Ag | Colorantes de n-aminopiridona. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1292454A (en) * | 1969-09-23 | 1972-10-11 | Ici Ltd | Dyestuffs |
| ES398433A1 (es) * | 1970-12-30 | 1975-06-16 | Oreal | Un procedimiento de preparacion de una composicion tintoreapara fibras queratinidas. |
| LU68988A1 (it) * | 1973-12-12 | 1975-08-20 |
-
1978
- 1978-05-25 GB GB22730/78A patent/GB1599627A/en not_active Expired
- 1978-11-17 JP JP14121878A patent/JPS54153830A/ja active Pending
- 1978-11-21 FR FR7832831A patent/FR2426717A2/fr active Granted
- 1978-11-22 BE BE191873A patent/BE872201R/xx active
- 1978-12-04 IT IT52174/78A patent/IT1158155B/it active
- 1978-12-07 CH CH1251778A patent/CH640875A5/de not_active IP Right Cessation
- 1978-12-11 DE DE19782853354 patent/DE2853354A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IT7852174A0 (it) | 1978-12-04 |
| IT1158155B (it) | 1987-02-18 |
| FR2426717A2 (fr) | 1979-12-21 |
| FR2426717B2 (it) | 1982-04-02 |
| DE2853354A1 (de) | 1979-11-29 |
| BE872201R (fr) | 1979-05-22 |
| JPS54153830A (en) | 1979-12-04 |
| GB1599627A (en) | 1981-10-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |