SU416941A3 - Способ получения 9,10-дигидро-9,10-этаноантрацена - Google Patents

Способ получения 9,10-дигидро-9,10-этаноантрацена

Info

Publication number: SU416941A3
Authority: SU; USSR - Soviet Union
Prior art keywords: residue; dihydro; group; hydroxy; aminoalkyl
Prior art date: 1969-01-03

Application number

SU1603689A

Other languages

English (en)

Russian (ru)

Original Assignee

Ииостранец Макс Вильхельм

Иностраниа фирма

Циба Гейги

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.)

1969-01-03

Filing date

1969-12-30

Publication date

1974-02-25

1969-12-30 Application filed by Ииостранец Макс Вильхельм, Иностраниа фирма, Циба Гейги filed Critical Ииостранец Макс Вильхельм

1974-02-25 Application granted granted Critical

1974-02-25 Publication of SU416941A3 publication Critical patent/SU416941A3/ru

Links

238000000034 method Methods 0.000 title description 6
-1 chlorine - Chemical compound 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
125000004103 aminoalkyl group Chemical group 0.000 description 8
239000001257 hydrogen Chemical group 0.000 description 8
229910052739 hydrogen Chemical group 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
WKZVETHZWWSRFB-UHFFFAOYSA-N 1-(methylaminomethyl)tetracyclo[6.6.2.02,7.09,14]hexadeca-2(7),3,5,9,11,13-hexaen-4-ol Chemical compound OC1=CC=2C3(C4=CC=CC=C4C(C2C=C1)CC3)CNC WKZVETHZWWSRFB-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000004423 acyloxy group Chemical group 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
230000003301 hydrolyzing effect Effects 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
VPPCQVCZKDIGGG-UHFFFAOYSA-N dibenzobicyclo[2.2.2]octadiene Chemical compound C12=CC=CC=C2C2CCC1C1=CC=CC=C12 VPPCQVCZKDIGGG-UHFFFAOYSA-N 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
KGMDODIDEQTIRA-UHFFFAOYSA-N 1,2-dihydrocyclobuta[a]anthracene Chemical compound C1=CC2=CC3=CC=CC=C3C=C2C2=C1CC2 KGMDODIDEQTIRA-UHFFFAOYSA-N 0.000 description 1
LQPGRFYMFROOOX-UHFFFAOYSA-N 1-[(dimethylamino)methyl]tetracyclo[6.6.2.02,7.09,14]hexadeca-2(7),3,5,9,11,13-hexaen-4-ol Chemical compound OC1=CC=2C3(C4=CC=CC=C4C(C2C=C1)CC3)CN(C)C LQPGRFYMFROOOX-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
XQMVBICWFFHDNN-UHFFFAOYSA-N 5-amino-4-chloro-2-phenylpyridazin-3-one;(2-ethoxy-3,3-dimethyl-2h-1-benzofuran-5-yl) methanesulfonate Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1.C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 XQMVBICWFFHDNN-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
XSMYSUNHQXJOON-UHFFFAOYSA-N OC1=CC=2C3(C4=CC=CC=C4C(C2C=C1)CC3)C=O Chemical compound OC1=CC=2C3(C4=CC=CC=C4C(C2C=C1)CC3)C=O XSMYSUNHQXJOON-UHFFFAOYSA-N 0.000 description 1
QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
229910001297 Zn alloy Inorganic materials 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004945 acylaminoalkyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
HIGRAKVNKLCVCA-UHFFFAOYSA-N alumine Chemical compound C1=CC=[Al]C=C1 HIGRAKVNKLCVCA-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
150000001845 chromium compounds Chemical class 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000007599 discharging Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910001092 metal group alloy Inorganic materials 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229940070891 pyridium Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1

Classifications

- G—PHYSICS
- G01—MEASURING; TESTING
- G01V—GEOPHYSICS; GRAVITATIONAL MEASUREMENTS; DETECTING MASSES OR OBJECTS; TAGS
- G01V3/00—Electric or magnetic prospecting or detecting; Measuring magnetic field characteristics of the earth, e.g. declination, deviation
- G01V3/08—Electric or magnetic prospecting or detecting; Measuring magnetic field characteristics of the earth, e.g. declination, deviation operating with magnetic or electric fields produced or modified by objects or geological structures or by detecting devices

Landscapes

Physics & Mathematics (AREA)
Engineering & Computer Science (AREA)
Remote Sensing (AREA)
Life Sciences & Earth Sciences (AREA)
Electromagnetism (AREA)
Environmental & Geological Engineering (AREA)
Geology (AREA)
General Life Sciences & Earth Sciences (AREA)
General Physics & Mathematics (AREA)
Geophysics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SU1603689A 1969-01-03 1969-12-30 Способ получения 9,10-дигидро-9,10-этаноантрацена SU416941A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1369A CH513108A (de)	1969-01-03	1969-01-03	Verfahren zur Herstellung neuer Amine

Publications (1)

Publication Number	Publication Date
SU416941A3 true SU416941A3 (ru)	1974-02-25

Family

ID=4177420

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1603689A SU416941A3 (ru)	1969-01-03	1969-12-30	Способ получения 9,10-дигидро-9,10-этаноантрацена

Country Status (2)

Country	Link
CH (5)	CH513107A (de)
SU (1)	SU416941A3 (de)

1969
- 1969-01-03 CH CH1879770A patent/CH513107A/de not_active IP Right Cessation
- 1969-01-03 CH CH1879970A patent/CH513811A/de not_active IP Right Cessation
- 1969-01-03 CH CH1879670A patent/CH532550A/de not_active IP Right Cessation
- 1969-01-03 CH CH1369A patent/CH513108A/de not_active IP Right Cessation
- 1969-01-03 CH CH1879870A patent/CH525180A/de not_active IP Right Cessation
- 1969-12-30 SU SU1603689A patent/SU416941A3/ru active

Also Published As

Publication number	Publication date
CH525180A (de)	1972-07-15
CH513108A (de)	1971-09-30
CH513107A (de)	1971-09-30
CH532550A (de)	1973-01-15
CH513811A (de)	1971-10-15

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