DE2207111C2 - 9-(3-Oxo-1-propenyl)-9,10-dihydro-9,10-äthano-anthracen-Verbindungen - Google Patents
9-(3-Oxo-1-propenyl)-9,10-dihydro-9,10-äthano-anthracen-VerbindungenInfo
- Publication number
- DE2207111C2 DE2207111C2 DE2207111A DE2207111A DE2207111C2 DE 2207111 C2 DE2207111 C2 DE 2207111C2 DE 2207111 A DE2207111 A DE 2207111A DE 2207111 A DE2207111 A DE 2207111A DE 2207111 C2 DE2207111 C2 DE 2207111C2
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- ethano
- propenyl
- oxo
- anthracene
- 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
- SEKAHXWZBXZWDA-UHFFFAOYSA-N 3-(9,10-ethano-9(10h)-anthryl)acrylaldehyde Chemical class C12=CC=CC=C2C2(C=CC=O)C3=CC=CC=C3C1CC2 SEKAHXWZBXZWDA-UHFFFAOYSA-N 0.000 title claims description 13
- -1 3-methylimino-1-propenyl Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- YOBVRYJTDYIIOK-UHFFFAOYSA-N 3-(4-chloro-1-tetracyclo[6.6.2.02,7.09,14]hexadeca-2(7),3,5,9,11,13-hexaenyl)prop-2-enal Chemical compound ClC1=CC=2C3(C4=CC=CC=C4C(C2C=C1)CC3)C=CC=O YOBVRYJTDYIIOK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- NLHDGEXLFCDTHQ-BJMVGYQFSA-N (e)-3-anthracen-9-ylprop-2-enal Chemical class C1=CC=C2C(/C=C/C=O)=C(C=CC=C3)C3=CC2=C1 NLHDGEXLFCDTHQ-BJMVGYQFSA-N 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 239000005977 Ethylene Substances 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 238000006359 acetalization reaction Methods 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- NZDMFGKECODQRY-UHFFFAOYSA-N Maprotiline hydrochloride Chemical compound Cl.C12=CC=CC=C2C2(CCCNC)C3=CC=CC=C3C1CC2 NZDMFGKECODQRY-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- IXNMOGHTIUHVSV-UHFFFAOYSA-N N-methyl-3-(1-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)prop-2-en-1-imine Chemical compound CN=CC=CC12C3=CC=CC=C3C(C=3C=CC=CC13)CC2 IXNMOGHTIUHVSV-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 235000019256 formaldehyde Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 2
- 235000015096 spirit Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical group C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- RVLPMOASZWJYHU-UHFFFAOYSA-N 3-anthracen-9-yl-N-methylprop-2-en-1-imine Chemical compound CN=CC=CC=1C2=CC=CC=C2C=C2C=CC=CC12 RVLPMOASZWJYHU-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
- BPZMYSHIRKBEKU-UHFFFAOYSA-N 9,10-ethanoanthracene-9(10h)-carbaldehyde Chemical compound C12=CC=CC=C2C2(C=O)C3=CC=CC=C3C1CC2 BPZMYSHIRKBEKU-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- QSLMDECMDJKHMQ-UHFFFAOYSA-N Maprotiline Chemical compound C12=CC=CC=C2C2(CCCNC)C3=CC=CC=C3C1CC2 QSLMDECMDJKHMQ-UHFFFAOYSA-N 0.000 description 1
- BBNBXLRSBFJQNO-UHFFFAOYSA-N N-methyl-3-(1-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)prop-2-en-1-amine hydrochloride Chemical compound Cl.CNCC=CC12C3=CC=CC=C3C(C=3C=CC=CC13)CC2 BBNBXLRSBFJQNO-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- YMNKUHIVVMFOFO-UHFFFAOYSA-N anthracene-9-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(C=CC=C3)C3=CC2=C1 YMNKUHIVVMFOFO-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- IFHUOEQJTQWFGJ-UHFFFAOYSA-N demethylmaprotiline Chemical compound C12=CC=CC=C2C2(CCCN)C3=CC=CC=C3C1CC2 IFHUOEQJTQWFGJ-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/44—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH257671A CH552548A (de) | 1971-02-23 | 1971-02-23 | Verfahren zur herstellung neuer aethanoanthracene. |
| CH66772 | 1972-01-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2207111A1 DE2207111A1 (de) | 1972-09-07 |
| DE2207111C2 true DE2207111C2 (de) | 1983-10-20 |
Family
ID=25685306
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2207111A Expired DE2207111C2 (de) | 1971-02-23 | 1972-02-16 | 9-(3-Oxo-1-propenyl)-9,10-dihydro-9,10-äthano-anthracen-Verbindungen |
| DE2265640A Expired DE2265640C2 (de) | 1971-02-23 | 1972-02-16 | 3-(9-Anthryl)-acrolein-Verbindungen und Verfahren zu deren Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2265640A Expired DE2265640C2 (de) | 1971-02-23 | 1972-02-16 | 3-(9-Anthryl)-acrolein-Verbindungen und Verfahren zu deren Herstellung |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3868421A (en:Method) |
| JP (1) | JPS5912649B1 (en:Method) |
| AT (2) | AT315160B (en:Method) |
| BE (1) | BE779663A (en:Method) |
| CA (1) | CA1021351A (en:Method) |
| DE (2) | DE2207111C2 (en:Method) |
| ES (1) | ES400020A1 (en:Method) |
| FR (1) | FR2126352B1 (en:Method) |
| GB (2) | GB1383333A (en:Method) |
| HU (1) | HU163516B (en:Method) |
| NL (2) | NL7202324A (en:Method) |
| SE (2) | SE384019B (en:Method) |
| SU (1) | SU451234A3 (en:Method) |
| YU (2) | YU35096B (en:Method) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2761883A (en) * | 1952-11-10 | 1956-09-04 | Shell Dev | Reduction of 9, 10 anthracene carbonylic adducts |
| NL127069C (en:Method) * | 1961-10-10 |
-
1972
- 1972-02-11 CA CA134,497A patent/CA1021351A/en not_active Expired
- 1972-02-11 US US225614A patent/US3868421A/en not_active Expired - Lifetime
- 1972-02-16 DE DE2207111A patent/DE2207111C2/de not_active Expired
- 1972-02-16 DE DE2265640A patent/DE2265640C2/de not_active Expired
- 1972-02-18 SE SE7201992A patent/SE384019B/xx unknown
- 1972-02-18 GB GB3619174A patent/GB1383333A/en not_active Expired
- 1972-02-18 GB GB762372A patent/GB1383332A/en not_active Expired
- 1972-02-21 YU YU433/72A patent/YU35096B/xx unknown
- 1972-02-21 ES ES400020A patent/ES400020A1/es not_active Expired
- 1972-02-22 AT AT143272A patent/AT315160B/de not_active IP Right Cessation
- 1972-02-22 NL NL7202324A patent/NL7202324A/xx active Search and Examination
- 1972-02-22 BE BE779663A patent/BE779663A/xx unknown
- 1972-02-22 HU HUCI1212A patent/HU163516B/hu unknown
- 1972-02-22 SU SU1752588A patent/SU451234A3/ru active
- 1972-02-22 AT AT10576/72*A patent/AT318596B/de not_active IP Right Cessation
- 1972-02-23 JP JP47018164A patent/JPS5912649B1/ja active Granted
- 1972-02-23 FR FR7206114A patent/FR2126352B1/fr not_active Expired
-
1975
- 1975-01-10 SE SE7500261A patent/SE430328B/xx not_active IP Right Cessation
-
1979
- 1979-06-11 YU YU01365/79A patent/YU136579A/xx unknown
-
1983
- 1983-09-26 NL NL8303286A patent/NL8303286A/nl not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| HU163516B (en:Method) | 1973-09-27 |
| DE2265640C2 (de) | 1983-04-07 |
| YU136579A (en) | 1980-10-31 |
| YU43372A (en) | 1980-03-15 |
| YU35096B (en) | 1980-09-25 |
| SE430328B (sv) | 1983-11-07 |
| SU451234A3 (ru) | 1974-11-25 |
| US3868421A (en) | 1975-02-25 |
| DE2207111A1 (de) | 1972-09-07 |
| NL7202324A (en:Method) | 1972-08-25 |
| AT318596B (de) | 1974-10-25 |
| NL8303286A (nl) | 1984-01-02 |
| FR2126352B1 (en:Method) | 1976-07-09 |
| GB1383333A (en) | 1974-02-12 |
| GB1383332A (en) | 1974-02-12 |
| SE7500261L (en:Method) | 1975-01-10 |
| SE384019B (sv) | 1976-04-12 |
| AT315160B (de) | 1974-05-10 |
| CA1021351A (en) | 1977-11-22 |
| BE779663A (fr) | 1972-06-16 |
| FR2126352A1 (en:Method) | 1972-10-06 |
| ES400020A1 (es) | 1975-06-16 |
| JPS5912649B1 (en:Method) | 1984-03-24 |
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