DE2731454A1 - Neue acetophenon-derivate und verfahren zu ihrer herstellung - Google Patents
Neue acetophenon-derivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2731454A1 DE2731454A1 DE19772731454 DE2731454A DE2731454A1 DE 2731454 A1 DE2731454 A1 DE 2731454A1 DE 19772731454 DE19772731454 DE 19772731454 DE 2731454 A DE2731454 A DE 2731454A DE 2731454 A1 DE2731454 A1 DE 2731454A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- compound
- formula
- hydrogen
- acetophenone
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 21
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical class CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- -1 arylsulfonyl chloride Chemical compound 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Chemical group 0.000 claims description 7
- PHKBTLWUWOTBOQ-UHFFFAOYSA-N phenacyl 2-methoxybenzenesulfonate Chemical compound COC1=CC=CC=C1S(=O)(=O)OCC(=O)C1=CC=CC=C1 PHKBTLWUWOTBOQ-UHFFFAOYSA-N 0.000 claims description 6
- 150000008062 acetophenones Chemical class 0.000 claims description 5
- 229910052736 halogen Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- XXDVKBYOLZQKJC-UHFFFAOYSA-N phenacyl 2-methoxy-4-methylbenzenesulfonate Chemical compound COC1=CC(C)=CC=C1S(=O)(=O)OCC(=O)C1=CC=CC=C1 XXDVKBYOLZQKJC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 3
- RTNIIFNCNTUUAH-UHFFFAOYSA-N phenacyl 2,6-dimethoxybenzenesulfonate Chemical compound COC1=CC=CC(OC)=C1S(=O)(=O)OCC(=O)C1=CC=CC=C1 RTNIIFNCNTUUAH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 3
- 229940067157 phenylhydrazine Drugs 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- HCBPHBQMSDVIPZ-UHFFFAOYSA-N methylcyclohexatriene Chemical compound CC1=CC=C=C[CH]1 HCBPHBQMSDVIPZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 239000012429 reaction media Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 11
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 6
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002475 indoles Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- GXGQIOUAJXWNFK-UHFFFAOYSA-N [4-(1h-indol-2-yl)-2-methoxyphenyl] benzenesulfonate Chemical compound COC1=CC(C=2NC3=CC=CC=C3C=2)=CC=C1OS(=O)(=O)C1=CC=CC=C1 GXGQIOUAJXWNFK-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- OJOBTAOGJIWAGB-UHFFFAOYSA-N acetosyringone Chemical compound COC1=CC(C(C)=O)=CC(OC)=C1O OJOBTAOGJIWAGB-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- FGEQCIOKNOXGOE-UHFFFAOYSA-N 4-(1h-indol-2-yl)-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2NC3=CC=CC=C3C=2)=C1 FGEQCIOKNOXGOE-UHFFFAOYSA-N 0.000 description 1
- 238000006674 Bischler reaction Methods 0.000 description 1
- 238000006783 Fischer indole synthesis reaction Methods 0.000 description 1
- 238000006641 Fischer synthesis reaction Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- FLALTECNJHSKPQ-UHFFFAOYSA-N [4-(1H-indol-2-yl)-2-methoxyphenyl] phenylmethanesulfonate Chemical compound COC=1C=C(C=CC=1OS(=O)(=O)CC1=CC=CC=C1)C=1NC2=CC=CC=C2C=1 FLALTECNJHSKPQ-UHFFFAOYSA-N 0.000 description 1
- UXOHQFTYDSTBJV-UHFFFAOYSA-N [4-(1h-indol-2-yl)-2-methoxyphenyl] methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C(OC)=CC(C=2NC3=CC=CC=C3C=2)=C1 UXOHQFTYDSTBJV-UHFFFAOYSA-N 0.000 description 1
- WIUNASOISWTCEL-UHFFFAOYSA-N [4-(2-bromo-1,1-dimethoxyethyl)-2-methoxyphenyl] benzenesulfonate Chemical compound COC1=CC(C(CBr)(OC)OC)=CC=C1OS(=O)(=O)C1=CC=CC=C1 WIUNASOISWTCEL-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7621581A FR2358389A1 (fr) | 1976-07-15 | 1976-07-15 | Nouveaux derives sulfonyles d'acetophenone, leur procede de preparation et leurs applications a la preparation de stabilisants pour resines thermoplastiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2731454A1 true DE2731454A1 (de) | 1978-01-19 |
Family
ID=9175737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772731454 Withdrawn DE2731454A1 (de) | 1976-07-15 | 1977-07-12 | Neue acetophenon-derivate und verfahren zu ihrer herstellung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4134909A (https=) |
| JP (1) | JPS5337640A (https=) |
| BE (1) | BE856618A (https=) |
| CH (1) | CH626334A5 (https=) |
| DE (1) | DE2731454A1 (https=) |
| FR (1) | FR2358389A1 (https=) |
| GB (1) | GB1541959A (https=) |
| NL (1) | NL7707418A (https=) |
| SE (1) | SE7708184L (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2724654B1 (fr) * | 1994-09-16 | 1997-12-12 | Roussel Uclaf | Nouveaux derives de l'acide gallique, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3818102A (en) * | 1970-03-09 | 1974-06-18 | Monsanto Co | Insecticidal sulfonates |
-
1976
- 1976-07-15 FR FR7621581A patent/FR2358389A1/fr active Granted
-
1977
- 1977-06-29 US US05/811,054 patent/US4134909A/en not_active Expired - Lifetime
- 1977-07-05 NL NL7707418A patent/NL7707418A/xx not_active Application Discontinuation
- 1977-07-08 GB GB7728857A patent/GB1541959A/en not_active Expired
- 1977-07-08 BE BE179184A patent/BE856618A/xx unknown
- 1977-07-12 DE DE19772731454 patent/DE2731454A1/de not_active Withdrawn
- 1977-07-14 SE SE7708184A patent/SE7708184L/xx not_active Application Discontinuation
- 1977-07-15 CH CH880677A patent/CH626334A5/fr not_active IP Right Cessation
- 1977-07-15 JP JP8553777A patent/JPS5337640A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2358389B1 (https=) | 1981-11-06 |
| NL7707418A (nl) | 1978-01-17 |
| BE856618A (fr) | 1978-01-09 |
| GB1541959A (en) | 1979-03-14 |
| CH626334A5 (https=) | 1981-11-13 |
| FR2358389A1 (fr) | 1978-02-10 |
| SE7708184L (sv) | 1978-01-16 |
| JPS5337640A (en) | 1978-04-06 |
| US4134909A (en) | 1979-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |