DE71312C - Process for the preparation of halogen and amidoacetophenone derivatives - Google Patents
Process for the preparation of halogen and amidoacetophenone derivativesInfo
- Publication number
- DE71312C DE71312C DENDAT71312D DE71312DA DE71312C DE 71312 C DE71312 C DE 71312C DE NDAT71312 D DENDAT71312 D DE NDAT71312D DE 71312D A DE71312D A DE 71312DA DE 71312 C DE71312 C DE 71312C
- Authority
- DE
- Germany
- Prior art keywords
- melts
- preparation
- halogen
- parts
- catechol
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims 4
- 238000002360 preparation method Methods 0.000 title claims 3
- 229910052736 halogen Inorganic materials 0.000 title description 9
- 150000002367 halogens Chemical class 0.000 title description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 20
- 239000000155 melt Substances 0.000 claims description 11
- WQGWDDDVZFFDIG-UHFFFAOYSA-N Pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 10
- -1 p-amidophenetol Chemical compound 0.000 claims description 7
- 229940079877 Pyrogallol Drugs 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- FOCAUTSVDIKZOP-UHFFFAOYSA-N Chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- KDPAWGWELVVRCH-UHFFFAOYSA-N Bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-Methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N Isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 1
- UWYZHKAOTLEWKK-UHFFFAOYSA-N Tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 210000001772 Blood Platelets Anatomy 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N Chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N Ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 210000004400 Mucous Membrane Anatomy 0.000 description 1
- 210000001331 Nose Anatomy 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L Platinum(II) chloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J Tin(IV) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/06—Alkylated phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
Description
PATENTAMPATENTAM
KAISERLICHESIMPERIAL
Durch Einwirkung von Chlor- oder Bromessigsäure auf Brenzkatechin oder Pyrogallol werden Halogenacetophenone dargestellt nach folgender Gleichung:By the action of chloro- or bromoacetic acid on catechol or pyrogallol Halogenacetophenones are represented according to the following equation:
C. Ä (O H), + ClCHtCO OH
■;-. = ClCH2COC6H2(O H)5 +H2O.
Die Halogenderivate reagiren leicht mit Basen unter Bildung von Amidoacetophenonen, z.B.:C. Ä (OH), + ClCHtCO OH
■; -. = ClCH 2 COC 6 H 2 (OH) 5 + H 2 O.
The halogen derivatives react easily with bases to form amidoacetophenones, e.g.
Cl CH2C OCn K, (O H)3 + Cn H, NH2 = CaH. NHCH2COC6H2(OH)3 + HCl. Cl CH 2 C OC n K, (OH) 3 + C n H, NH 2 = C a H. NHCH 2 COC 6 H 2 (OH) 3 + HCl.
Beispiel i. Zur Herstellung von Chlor-· acetopyrogallol werden 50 Theile Pyrogallol, 40 Theile Chloressigsäure und 40 Theile Phosphproxychlorid erwärmt, bis die Schmelze ' stürmisch Chlorwasserstoff entwickelt. Man giebt hierauf das doppelte Volumen heifsen Wassers hinzu und filtrirt. Das Filtrat erstarrt zu einem Krystallbrei von langen farblosen Nadeln, welche aus Wasser umkrystallisirt werden. , ; Example i. To prepare chloroacetopyrogallol, 50 parts of pyrogallol, 40 parts of chloroacetic acid, and 40 parts of phosphproxychloride are heated until the melt violently evolves hydrogen chloride. Double the volume of hot water is then added and the mixture is filtered. The filtrate solidifies to a crystalline pulp of long, colorless needles, which are recrystallized from water. , ;
Schmp. 1680C; leicht löslich in Alkohol, Aether und heifsem Wasser. Greift Schleimhäute stark an.Mp. 168 0 C; Easily soluble in alcohol, ether and hot water. Severely attacks mucous membranes.
Bei· dieser Reaction kann man das Pyrogallol durch Brenzkatechin ersetzen, die Chloressigsäure durch Bromessigsäure, beide Halogenfettsäuren durch ihre Salze, Ester, Chloride, Anhydride oder Amide, das Phosphoroxychlorid durch die anderen üblichen Condensationsmittel, z. B. Zink- oder Zinnchlorid oder Schwefelsäure. Die Reaction gestaltet sich dann ganz so, wie sie von Nencki und dessen Schülern' (Journal für prakt. Chemie, Bd. 23, S, 147 und 538) beschrieben und später im Patent Nr. 49149 benutzt worden ist.In this reaction the pyrogallol can be replaced by pyrocatechol, the chloroacetic acid by bromoacetic acid, both halogen fatty acids by their salts, esters, chlorides, Anhydrides or amides, the phosphorus oxychloride by the other common condensation agents, z. B. zinc or tin chloride or sulfuric acid. The reaction shapes then just as they were told by Nencki and his students' (Journal for Practical Chemistry, Vol. 23, S, 147 and 538) and later used in Patent No. 49149.
Beispiel 2. 10 Theile Pyrogallol und. '.. 15 Theile Chloressigsä.üre oder .16 Theile Chloracetamid oder 18 Theile Chloressigsäureäthylester werden geschmolzen. Zur Schmelze werden langsam 20 Theile Chlorzink gegeben. Die Temperatur darf nie über 1 500 C. steigen. Man erhitzt, so lange, bis bei dem Umkrystallisiren einer herausgenommenen Probe mit Wasser die ausgeschiedenen Krystalle sich nichtExample 2. 10 parts pyrogallol and. '.. 15 parts Chloressigsä.üre or chloroacetamide .16 parts or 18 parts of ethyl chloroacetate are melted. 20 parts of zinc chloride are slowly added to the melt. The temperature must never rise above 1 50 0 C. It is heated until the crystals which have separated out do not separate themselves when a sample which has been taken out is recrystallized with water
weheFvennehrenr Hierauf wird die SchmelzeWoheFvennehrenr Thereupon the melt
in kochendem Wasser gelöst. ~*ei—dem- Er-., kalten scheidet sich das Chloracetopyrogallol in langen Nadeln ab. . _ .dissolved in boiling water. ~ * ei — dem- er-., cold the chloroacetopyrogallol separates into long needles. . _.
Bei Anwendung der Säurechloride und Anhydride kann das Condensationsmittel auch weggelassen werden. . . .When using the acid chlorides and anhydrides, the condensation agent can also can be omitted. . . .
Beispiel 3. 10 Theile Brenzkatechin und, 10 Theile Chloracetylchlorid (oder 8 Theile Chloracctanhydrid) werden vorsichtig bis zur starken Salzsa'uregasentwickeluHg erwärmt.Example 3. 10 parts catechol and 10 parts chloroacetyl chloride (or 8 parts Chloracctic anhydride) are carefully warmed up until the development of hydrochloric acid gas is strong.
Die Reaction geht von selbst zu Ende. Das Reactionsproduct wird aus Wasser, eventuell unter Benutzung von Thierkohle umkrystallisirt. Stark zum Niefsen reizend;. farblose. Nadeln vom Schmp. 1730 C;The reaction comes to an end by itself. The reaction product is recrystallized from water, possibly with the use of animal charcoal. Strongly irritating to the nose. colorless. Needles of mp 173 0C.;
Es wurden so folgende neue Stoffe hergestellt:The following new fabrics were produced in this way:
Monochloracetobrenzkatechin Cl CH2 COCnHx (O H)2, Schmp. 1730 C:\;.; Monobromacetobrenzkatechin Br C-H., CO C„ H1 (O H)2, Schmp. 170 C; Monochloracetopyrogallol Cl CH2CO Cn H1 (O Η)Ά, Schmp. i68° C.-, Monobromacetopyrogallol Br C H2 C OC1. H2(O H),, Schmp. 158 bis ι 590 C.Monochloroacetobrenzcatechol Cl CH 2 COC n H x (OH) 2 , m.p. 173 0 C: \;.; Monobromoaceto catechol Br CH., CO C "H 1 (OH) 2 , m.p. 170 C; Monochloroacetopyrogallol Cl CH 2 CO C n H 1 (O Η) Ά , melting point i68 ° C.-, monobromoacetopyrogallol Br CH 2 C OC 1 . H 2 (OH) ,, m.p. 158 to ι 59 0 C.
Das in diesen Ketonen enthaltene Halogen kann schon durch Kochen mit Wasser abgespalten werden, noch leichter bei Gegenwart kohlensaurer oder ätzender Alkalien oder Erdalkalien. Aus den obigen Stoffen Nr. 3 und entsteht dabei eine Anhydroverbindung, das Dioxyphenylmethylxanthon:The halogen contained in these ketones can be split off by boiling with water, even more easily in the presence carbonic or caustic alkalis or alkaline earths. From the above substances no. 3 and This creates an anhydro compound, dioxyphenylmethylxanthone:
(OHJ2 C6 H^^ CH2, Schmp. 2240C. (OHJ 2 C 6 H ^^ CH 2 , m.p. 224 0 C.
Mit Stickstoff basen reagiren diese Halogenketone unter Bildung von Amidoketonen.These halogen ketones react with nitrogen bases with the formation of amidoketones.
Z. B.:E.g .:
i. eine concentrirte alkoholische Lösung von Chloracetobrenzkatechin (17 Theile) wird mit Chinolin (13 Theile) versetzt. Die Mischung erwärmt sich und erstarrt zu einem Krystallbrei von salzsaurem Chinolylacetobrenzkatechin:i. a concentrated alcoholic solution of chloroaceto-catechol (17 parts) is added Quinoline (13 parts) added. The mixture heats up and solidifies to form a crystalline slurry of hydrochloric acid quinolylaceto catechol:
C9H7N+ ClCH2COC6H3(OH)2 = C0H7N-^n COC6H3(OHJ2. C 9 H 7 N + ClCH 2 COC 6 H 3 (OH) 2 = C 0 H 7 N- ^ n COC 6 H 3 (OHJ 2 .
i. 2.i. 2.
3·3 ·
4.4th
5· 6. 5 6.
Das Product krystallisirt aus Alkohol in' Prismen vom Schmp. 1290 C. und bildet mit Platinchlorid ein Doppclsalz;The product crystallizes from alcohol in 'prisms of mp 129 0 C. and forms with platinum chloride Doppclsalz.
2. man erwärmt eine Mischung von i8Theilen Chloracetopyrogallol und 18 Theilen Anilin, am besten unter Verdünnung (z.B. mit Alkohol), kurze Zeit im Wasserbade. .. .2. A mixture of 18 parts is heated Chloroacetopyrogallol and 18 parts aniline, preferably diluted (e.g. with alcohol), a short time in the water bath. ...
Die Reaction vollzieht sich nach der Gleichung: . : The reaction takes place according to the equation:. :
C0 H2 (O H)3 COCH2 Cl + 2 C6 H5NH2 = C6H2(O H), C OC H2N H C6H. . + C6H0NH2-HCl. C 0 H 2 (OH) 3 COCH 2 Cl + 2 C 6 H 5 NH 2 = C 6 H 2 (OH), C OC H 2 NHC 6 H.. + C 6 H 0 NH 2 -HCl.
Man erhält das Reactionsproduct aus Benzol in Blättchen vom Schmp. 1320.This gives the Reactionsproduct of benzene in platelets of mp. 132 0th
In gleicher Weise haben wir auf die obigen Halogenketone folgende Basen einwirken lassen:In the same way we have to the above Let the halogen ketones take effect:
Dimethylamin, Anilin, Mono- und Dimethylanilin, p-Amidophenetol, Pyridin, Chinolin, Piperidin, Tetrahydrochinolin, Isotetrahydrochinolin. :.'■..··Dimethylamine, aniline, mono- and dimethylaniline, p-amidophenetol, pyridine, quinoline, Piperidine, tetrahydroquinoline, isotetrahydroquinoline. :. '■ .. ··
Dabei wurden folgende Amidoketone erhalten:
Dimethylamidoacetobrenzkatechin (C HJ2 N-CH2CO C6 H3 (O HJ, The following amidoketones were obtained:
Dimethylamidoaceto catechol (C HJ 2 N-CH 2 CO C 6 H 3 (O HJ,
die Oxalate schmelzen bei 2 3 ο bis 2400 C.the oxalates melt at 2 3 ο to 240 0 C.
unter Verkohlung;under charring;
Dimethylamidoacetopyrogallol (CH3J2 N-CH2CO C6 H2 (O H)3 Dimethylamidoacetopyrogallol (CH 3 J 2 N-CH 2 CO C 6 H 2 (OH) 3
Anilidoacetobrenzkatechin C6 H5NH- C H2C O C0 H3 (O H)2, Schmp. 16o° C.;
Anilidoacetopyrogallol C0 H5NH- C Hn C OC6 H2 (O H)3, Schmp. 132° C.;Anilidoaceto catechol C 6 H 5 NH-CH 2 CO C 0 H 3 (OH) 2 , m.p. 160 ° C .;
Anilidoacetopyrogallol C 0 H 5 NH-CH n C OC 6 H 2 (OH) 3 , m.p. 132 ° C .;
Monomethylanilidoacetobrenzkatechin ^Ui ^' ^ H2 COC6 H3 (O H)2, Schmp. 1530 C; MonomethylanilidoacetopyrogallolMonomethylanilidoacetobrenzkatechin ^ U ^ '^ H 2 COC 6 H 3 (OH) 2, mp 153 0C.; Monomethylanilidoacetopyrogallol
N-C H2COC6H2 (O H)3, Schmp. i68° C.; NC H 2 COC 6 H 2 (OH) 3 , m.p. 168 ° C .;
— Halogen .- halogen.
N-, C H2GOC6 H3 (O H)2, Chlorid schmilzt N-, CH 2 GOC 6 H 3 (OH) 2 , chloride melts
9· 10.9 · 10.
Dlmethylanilidoacetobrenzkatechin bei 1820 C; . : ·Dlmethylanilidoacetobrenzcatechol at 182 0 C; . : ·
!CH)')—Hal°gen . ! CH) ') - Hal ° g en .
Dimethylanilidoacetopyrogallol 'Jr £h N ■ C H2 C OC6H2(O H)3, Chlorid schmilzt beiDimethylanilidoacetopyrogallol 'Jr £ h N · CH 2 C OC 6 H 2 (OH) 3 , chloride melts at
·, ■■ ■ ^e ■"& ) " ;.·, ■■ ■ ^ e ■ "& )"; .
1300C. . , ■;■.··■;· ;130 0 C.. , ■; ■. ·· ■; ·;
p-Aethoxyanilidoacetobrenzkatechin C2 H. O C6 Hi N H · C H2 C O C6H3 (O H)2, Schmelzpunkt
1050 C; .
p-Aethoxyanilidöacetopyrogallol CfH& O C6 i74 NH- CH2C OC6 H2(OH)3, Schmelzpunktp-Aethoxyanilidoacetobrenzkatechol C 2 H. OC 6 H i NH · CH 2 COC 6 H 3 (OH) 2 , melting point 105 0 C; .
p-Aethoxyanilidoacetopyrogallol CfH & O C 6 i7 4 NH-CH 2 C OC 6 H 2 (OH) 3 , melting point
144° C; -144 ° C; -
11. Pyridylacetobrenzkatechin C5 H5 N 11. Pyridylaceto catechol C 5 H 5 N
— Halogen- halogen
12.12th
13· 14.13 14.
15. 16.15-16
19.19th
CH2COC6H3 (O H)2, das Chlorid verkohlt bei 2650 C.;. : ;: ■.■'. ·.■/·■ . ■ . ■- . , ■ ". '·. ■:■■-■■. ■ ■'" '■■■' ■'■ CH 2 COC 6 H 3 (OH) 2 , the chloride carbonizes at 265 0 C .;. :; : ■. ■ '. ·. ■ / · ■. ■. ■ -. , ■ ". '·. ■: ■■ - ■■. ■ ■'"'■■■' ■ '■
Pyridylacetopyrogallol Cr H N\"7^ζ^α^'>^'%~~α-'τ7Λ-τ^\- -j--· r»i-+ -j ι μ Yu · ο or· Pyridylacetopyrogallol C r HN \ "7 ^ ζ ^ α ^ '>^'% ~~ α-'τ7Λ-τ ^ \ - -j-- · r» i- + -j ι μ Yu · ο or ·
J J ■ ^o 0,0 j CH2 C OC6 H, (JTHJ3, das ChTond-sdimilzl -bei_j 8cr_G. ;■ JJ ■ ^ o 0,0 j CH 2 C OC 6 H, (JTHJ 3 , das ChTond-sdimilzl -bei_j 8cr_G.; ■
Piperidylacetobrenzkatechin C, H10 N- C H2 C OC1. H3 (O H)n, Schmp. 1780 C.;
Piperidylacetopyrogallol C5H1nN-CH2CO C6 H2 (O H)3, S'chmp. 1700C;Piperidylaceto catechol C, H 10 N- CH 2 C OC 1 . H 3 (OH) n, mp. 178 0 C .;
Piperidylacetopyrogallol C 5 H 1n N-CH 2 CO C 6 H 2 (OH) 3 , mp. 170 0 C;
Chinolylacetobrenzkatechin Halogen —1 N' CHi COCo Hi(0H)ii Chlorid schmilzt bei 1290 C; ' ; : - . ■ · ■■'.■■ ■ .'■. ■ ■■' ; . \: ■■■_;■ ■■·.■-. Quinolylaceto-catechol Halogen-1 N 'CHi COC o H i ( OH ) ii Chloride melts at 129 0 C; '; : - . ■ · ■■ '. ■■ ■.' ■. ■ ■■ '; . \: ■■■ _; ■ ■■ ·. ■ -.
Chiriolylacetopyrogallol „", ^ N-CH2COC6H2(OHJ3, Chlorid schmilzt beiChiriolylacetopyrogallol "", ^ N-CH 2 COC 6 H 2 (OHJ 3 , chloride melts at
1040 C.;:. ■ ° 104 0 C .; : . ■ ° ■. . ' " .■;'■' ■■.■:■■■ "■■■ . V■. . '". ■;' ■ '■■. ■: ■■■" ■■■. V.
u. 18. Tetrahydrochinolyl- und isochinolylacetobrenzkatechin C11 H1nN-CHn C OC6H3(OHJ2, and 18.Tetrahydroquinolyl and isoquinolylacetobrenzcatechol C 11 H 1n N-CH n C OC 6 H 3 (OHJ 2 ,
Schmp. des Chinolylproducts 1050C, Schmp. des Chlorids vom. Isoproduct 260 C.;
u. 20. Tetrahydrochinolyl- und isochinolylacetopyrogallol C,, UT10 N - C H2 CO C6 H2 (O H)3, Mp. Of the quinolyl product 105 0 C, mp. Of the chloride from. Isoproduct 260 C .;
and 20. Tetrahydroquinolyl and isoquinolylacetopyrogallol C ,, UT 10 N - CH 2 CO C 6 H 2 (OH) 3 ,
Schmp. des Chinolylproducts .1440C. . . , ; .,M.p. of the quinolyl product .144 0 C.. . ,; .,
Diese neuen Halogen- und Amidoketone sollen als Arzneistoffe dienen. , , . ;These new halogen and amido ketones are said to serve as drugs. ,,. ;
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE71312C true DE71312C (en) |
Family
ID=344626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT71312D Expired - Lifetime DE71312C (en) | Process for the preparation of halogen and amidoacetophenone derivatives |
Country Status (1)
| Country | Link |
|---|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2945064A (en) * | 1958-04-29 | 1960-07-12 | Merck & Co Inc | 2, 4-dihydroxy-3-methylphenacylamine, 2-hydroxy-4-methoxy-3-methylphena-cylamine andprocesses of preparing the same |
-
0
- DE DENDAT71312D patent/DE71312C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2945064A (en) * | 1958-04-29 | 1960-07-12 | Merck & Co Inc | 2, 4-dihydroxy-3-methylphenacylamine, 2-hydroxy-4-methoxy-3-methylphena-cylamine andprocesses of preparing the same |
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