DE149748C - - Google Patents
Info
- Publication number
- DE149748C DE149748C DENDAT149748D DE149748DA DE149748C DE 149748 C DE149748 C DE 149748C DE NDAT149748 D DENDAT149748 D DE NDAT149748D DE 149748D A DE149748D A DE 149748DA DE 149748 C DE149748 C DE 149748C
- Authority
- DE
- Germany
- Prior art keywords
- melts
- found
- ferric chloride
- amino
- nitrobenzaldehyde
- 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.)
- Active
Links
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000155 melt Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GSXUXSXBEUJRAJ-UHFFFAOYSA-N 4-bromo-2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1C=O GSXUXSXBEUJRAJ-UHFFFAOYSA-N 0.000 description 1
- MZPNQUMLOFWSEK-UHFFFAOYSA-N 4-chloro-2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1C=O MZPNQUMLOFWSEK-UHFFFAOYSA-N 0.000 description 1
- GEXSYMYVUXRCKI-UHFFFAOYSA-N N-[(4-amino-2-nitrophenyl)methylidene]hydroxylamine Chemical compound NC1=CC=C(C=NO)C([N+]([O-])=O)=C1 GEXSYMYVUXRCKI-UHFFFAOYSA-N 0.000 description 1
- OTIKYRVPXSEIPV-UHFFFAOYSA-N acetic acid;phenylhydrazine Chemical compound CC(O)=O.NNC1=CC=CC=C1 OTIKYRVPXSEIPV-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- -1 nitroaminobenzaldoxime Chemical compound 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Es wurde gefunden, daß sich p-Halogen-onitrobenzaldehyd in bequemer Weise aus demIt was found that p-halo-onitrobenzaldehyde conveniently from the
, p-Amino-o-nitrobenzaldoxim (vergl. Ber. d. D. ehem. Ges. XXXV, S. 1234) herstellen läßt, wenn man es mit wäßriger Chlor- oder Bromwasserstoffsäure und Eisenchlorid zum Sieden erhitzt. Es findet alsdann 1. Abspaltung der Oximgruppe und gleichzeitig 2. Ersatz der Aminogruppe durch Chlor bezw. Brom statt., p-Amino-o-nitrobenzaldoxime (see Ber. d. D. former Ges. XXXV, p. 1234) can be produced, when it is mixed with aqueous hydrochloric or hydrobromic acid and ferric chloride Boiling heated. It then finds 1. cleavage of the oxime group and at the same time 2. replacement the amino group by chlorine respectively. Bromine instead.
Das Verfahren sei in folgenden Beispielen erläutert:The procedure is explained in the following examples:
i. 36 g Nitroaminobenzaldoxim werden in 500 ecm konzentrierter Salzsäure und 165 ecm 10 prozentiger Eisenchloridlösung so lange mit Wasserdampf behandelt, bis das übergehende Destillat mit essigsaurem Phenylhydrazin nur noch schwach reagiert. Mit den Wasserdämpfen verflüchtigt sich der Aldehyd äußerst leicht und scheidet sich im Kondensat zum größeren Teil in fester Form ab; der andere Teil kann der wäßrigen Lösung leicht durch Extraktion entzogen werden. Der entstandene p-Chlor-o-nitrobenzaldehyd ist bereits früher (vergl. Patentschrift 128727, Kl. 22) beschrieben worden. Er schmilzt bei 67 bis 68° und liefert bei der ' Analyse stimmende Zahlen:i. 36 g of nitroaminobenzaldoxime are in 500 ecm concentrated hydrochloric acid and 165 ecm Treated 10 percent ferric chloride solution with steam until the passing over Distillate only reacts weakly with acetic acid phenylhydrazine. The evaporates with the water vapors Aldehyde extremely light and separates in the condensate for the most part in solid form away; the other part can easily be removed from the aqueous solution by extraction. The resulting p-chloro-o-nitrobenzaldehyde is already earlier (see patent specification 128727, class 22). It melts at 67 to 68 ° and delivers at the ' Analysis of correct numbers:
C7H4O3NCl Ber. C 45,2s H 2,16 N 7,55, C 7 H 4 O 3 NCl calc . C 45.2s H 2.16 N 7.55,
Gef. C 45,38 H 2,35 N 7,ιΊ. Found C 45.38 H 2.35 N 7, ι Ί .
Sein Phenylhydrazon schmilzt bei 176 bis 177°, sein Semicarbazon bei 269 bis 270°.Its phenylhydrazone melts at 176 to 177 °, its semicarbazone at 269 to 270 °.
2. Man ersetzt die Salzsäure des Beispiels 1 durch Bromwasserstoffsäure und verfährt im übrigen ebenso, wie eben angegeben. Der mit den Wasserdämpfen übergehende, bisher noch nicht dargestellte p-Brom-o-nitrobenzaldehyd schmilzt nach dem Umkristallisieren aus verdünntem Alkohol bei 97 bis 98° und lieferte bei der Analyse folgende 7.?ία\<ίη: 2. The hydrochloric acid of Example 1 is replaced by hydrobromic acid and the rest of the procedure is the same as just stated. The p-bromo-o-nitrobenzaldehyde, which has not yet been shown and which passes over with the water vapors, melts after recrystallization from dilute alcohol at 97 to 98 ° and gave the following analysis:
C7H4O3NBr Ber. C 36,53 Z/ 1,74 N 6,09, Gef. C 36,95 H 2,02 JV 6,36. Das Phenyhydrazon schmilzt bei 181 bis 1820. C 7 H 4 O 3 NBr calc . C 36.53 Z / 1.74 N 6.09, found C 36.95 H 2.02 JV 6.36. The phenyhydrazone melts at 181 to 182 0 .
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE149748C true DE149748C (en) |
Family
ID=416734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT149748D Active DE149748C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE149748C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2517150A1 (en) * | 1974-04-18 | 1975-10-30 | Mitsubishi Chem Ind | PHOTO-SENSITIVE MEASURES FOR ELECTROPHOTOGRAPHY |
-
0
- DE DENDAT149748D patent/DE149748C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2517150A1 (en) * | 1974-04-18 | 1975-10-30 | Mitsubishi Chem Ind | PHOTO-SENSITIVE MEASURES FOR ELECTROPHOTOGRAPHY |
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