JPS6121943B2 - - Google Patents

Info

Publication number: JPS6121943B2
Authority: JP; Japan
Prior art keywords: anthracene; compound; hours; formula; methylimino
Prior art date: 1971-02-23
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

Application number

JP58171437A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5984857A (ja

Inventor

Betsuku Deiita

Berunasukoni Raimonto

Shenkeru Karuru

Uiruherumu Matsukusu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date 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 date listed.)

1971-02-23

Filing date

1983-09-19

Publication date

1986-05-29

1983-09-19 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1984-05-16 Publication of JPS5984857A publication Critical patent/JPS5984857A/ja

1986-05-29 Publication of JPS6121943B2 publication Critical patent/JPS6121943B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 12
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
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 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
NLHDGEXLFCDTHQ-BJMVGYQFSA-N (e)-3-anthracen-9-ylprop-2-enal Chemical compound C1=CC=C2C(/C=C/C=O)=C(C=CC=C3)C3=CC2=C1 NLHDGEXLFCDTHQ-BJMVGYQFSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 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
239000003054 catalyst Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001816 cooling 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
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
-1 ethenyl ester Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000000034 method Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000000047 product Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP58171437A 1971-02-23 1983-09-19 ９−（３−メチルイミノ−１−プロペニル）‐アントラセンの製法 Granted JPS5984857A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH257671A CH552548A (de)	1971-02-23	1971-02-23	Verfahren zur herstellung neuer aethanoanthracene.
CH2576/71		1971-02-23
CH667/72		1972-01-17

Publications (2)

Publication Number	Publication Date
JPS5984857A JPS5984857A (ja)	1984-05-16
JPS6121943B2 true JPS6121943B2 (de)	1986-05-29

Family

ID=4236901

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
JP56088325A Expired JPS5915892B2 (ja)	1971-02-23	1981-06-10	３−（９−アンスリル）−アクロレインの製法
JP58171438A Expired JPS6014016B2 (ja)	1971-02-23	1983-09-19	９−（３−メチルアミノ−１−プロペニル）−アントラセンの製法
JP58171437A Granted JPS5984857A (ja)	1971-02-23	1983-09-19	９−（３−メチルイミノ−１−プロペニル）‐アントラセンの製法

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
JP56088325A Expired JPS5915892B2 (ja)	1971-02-23	1981-06-10	３−（９−アンスリル）−アクロレインの製法
JP58171438A Expired JPS6014016B2 (ja)	1971-02-23	1983-09-19	９−（３−メチルアミノ−１−プロペニル）−アントラセンの製法

Country Status (2)

Country	Link
JP (3)	JPS5915892B2 (de)
CH (2)	CH552548A (de)

1971
- 1971-02-23 CH CH257671A patent/CH552548A/de not_active IP Right Cessation
- 1971-02-23 CH CH871773A patent/CH544732A/de not_active IP Right Cessation
1981
- 1981-06-10 JP JP56088325A patent/JPS5915892B2/ja not_active Expired
1983
- 1983-09-19 JP JP58171438A patent/JPS6014016B2/ja not_active Expired
- 1983-09-19 JP JP58171437A patent/JPS5984857A/ja active Granted

Also Published As

Publication number	Publication date
JPS57126439A (en)	1982-08-06
JPS6014016B2 (ja)	1985-04-11
JPS5980639A (ja)	1984-05-10
JPS5915892B2 (ja)	1984-04-12
JPS5984857A (ja)	1984-05-16
CH552548A (de)	1974-08-15
CH544732A (de)	1974-01-15

Publication	Publication Date	Title
US2441069A (en)	1948-05-04	2-amino-methyl-indenes and their production
Snyder et al.	1948	An alkylation with the methiodide of 1-methyl-3-dimethylaminomethylindole (1-methylgramine)
Boekelheide et al.	1949	Curariform Activity and Chemical Structure. V. 1 Syntheses in the Quinolizidine Series2
Overberger et al.	1957	Azo Compounds. 1 Oxidation of 1, 1-Disubstituted Hydrazines. The Synthesis and Oxidation of cis-and trans-1-Amino-2, 6-diphenylpiperidine. A New Stereospecific Ring Closure
US2441935A (en)	1948-05-18	Imidazolidones and method for their manufacture
US3408396A (en)	1968-10-29	alpha-cyclohexyl-3, 4-disubstituted-phenyl acetamides
US3100775A (en)	1963-08-13	alpha-phenyl(pyridyl or piperidyl)alkyl esters of (chloro or lower alkoxy)-benzoic acids and congeners
US2941002A (en)	1960-06-14	Beta-hydroxy carboxylic acid amides substituted at the nitrogen atom
US3168567A (en)	1965-02-02	Hindered alkyl and alkylene secondary amines
Bergmann et al.	1951	Investigations in the Acetylene Series. I. The Reactions of 3-Methyl-1-butyn-3-ol with Phosphorus Trichloride and of 3-Methyl-3-buten-1-yne with Hydrochloric Acid
US3096244A (en)	1963-07-02	Substituted butyric acid amide and analgesia
US3166570A (en)	1965-01-19	Derivatives of benzo[e] isoindoline and their preparation
US2589378A (en)	1952-03-18	Phenyl-piperidino-coumarans
Koelsch	1943	A Synthesis of 4-Phenylpiperidines
US3028394A (en)	1962-04-03	9-phenyl octahydroindole compounds and process of making same
US2782191A (en)	1957-02-19	Nitrogen containing carbinols
Burger et al.	1950	Amino Derivatives of 2, 2-Diphenylcyclohexanone. I1
US2980683A (en)	1961-04-18	Process for preparing beta-substitutedethyl piperazines
US3006971A (en)	1961-10-31	Preparation of bicyclic nitro compounds
SU425387A3 (ru)	1974-04-25	СПОСОБ ПОЛУЧЕНИЯ N,N'-5ЯC-(a-OKCИAЛKИЛ) ЭТИЛЕНДИАМИНА
US3860652A (en)	1975-01-14	8-Aminoalkyl substituted dibenzobicyclo {8 3.2.1{9 {0 octadienes
US2761862A (en)	1956-09-04	Process for the manufacture of xanthine derivatives
JPS5915892B2 (ja)	1984-04-12	３−（９−アンスリル）−アクロレインの製法
US2795592A (en)	1957-06-11	Substituted tetrahydrofurfural and substituted tetrahydrofurfuryl alcohol
Walters et al.	1964	Condensation of Formaldehyde with Reissert Compounds