DE3033003C2 - Process for the preparation of optionally nucleus-substituted N-(3-aminophenyl)glycolic acid amides - Google Patents
Process for the preparation of optionally nucleus-substituted N-(3-aminophenyl)glycolic acid amidesInfo
- Publication number
- DE3033003C2 DE3033003C2 DE19803033003 DE3033003A DE3033003C2 DE 3033003 C2 DE3033003 C2 DE 3033003C2 DE 19803033003 DE19803033003 DE 19803033003 DE 3033003 A DE3033003 A DE 3033003A DE 3033003 C2 DE3033003 C2 DE 3033003C2
- Authority
- DE
- Germany
- Prior art keywords
- glycolic acid
- substituted
- aminophenyl
- acid amides
- preparation
- 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
- BIYQLXLSSLKTNE-UHFFFAOYSA-N n-(3-aminophenyl)-2-hydroxyacetamide Chemical class NC1=CC=CC(NC(=O)CO)=C1 BIYQLXLSSLKTNE-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 8
- 150000004988 m-phenylenediamines Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229920000954 Polyglycolide Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- ZULJARDNKHCAPA-UHFFFAOYSA-N 2-hydroxy-n-(3-nitrophenyl)acetamide Chemical class OCC(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZULJARDNKHCAPA-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- -1 methoxy, ethoxy, methyl Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000004986 phenylenediamines Chemical group 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 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
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von gegebenenfalls kernsubstituierten N-(3-Aminophenyl-)- glykolsäureamiden, dadurch gekennzeichnet, daß man m-Phenylendiamine in wäßrigem Medium, gegebenenfalls unter Zusatz von Mineralsäuren, mit Glykolsäure bei Temperaturen von etwa 80° bis 130°C umsetzt.The invention relates to a process for the preparation of optionally nucleus-substituted N-(3-aminophenyl)glycolic acid amides, characterized in that m-phenylenediamines are reacted with glycolic acid at temperatures of about 80° to 130°C in an aqueous medium, optionally with the addition of mineral acids.
Ein Zusatz von Mineralsäure wie Salzsäure oder Schwefelsäure, vorzugsweise in etwa molaren Mengen bezogen auf das Phenylendiamin begünstigt dabei die Bildung des monoacylierten Produktes.The addition of mineral acid such as hydrochloric acid or sulfuric acid, preferably in approximately molar amounts relative to the phenylenediamine, promotes the formation of the monoacylated product.
Die Umsetzung erfolgt in wäßriger Lösung vorzugsweise bei Temperaturen zwischen 100° und 110°C.The reaction takes place in aqueous solution preferably at temperatures between 100° and 110°C.
N-(3-Aminophenyl-)glykolsäureamide dienen unter anderem als Farbstoffzwischenprodukte (vgl. z. B. deutsche Patentschrift 8 63 973). N-(3-aminophenyl)glycolic acid amides serve, among other things, as dye intermediates (cf., for example, German Patent Specification 8 63 973).
Sie wurden bislang durch Reduktion der entsprechenden N-(3-Nitrophenyl-)glykolsäureamide hergestellt. Diese wiederum werden durch Umsetzung von 3-Nitroanilinen mit Polyglykolid oder Chloracetylchlorid mit anschließendem Austausch des ω-Chloratoms gegen die OH-Gruppe erhalten. Die Umsetzung mit dem Polyglykolid ist sicherheitstechnisch bedenklich, beim Austausch des ω -Chloratoms wird der Acetylrest teilweise wieder abgespalten.They have previously been produced by reducing the corresponding N-(3-nitrophenyl)glycolic acid amides. These in turn are obtained by reacting 3-nitroanilines with polyglycolide or chloroacetyl chloride and then replacing the ω- chlorine atom with the OH group. The reaction with the polyglycolide is questionable from a safety point of view, as the acetyl residue is partially split off again when the ω- chlorine atom is replaced.
Als Ausgangsprodukte eignen sich neben dem unsubstituierten m-Phenylendiamin auch die durch übliche Substituenten substituierte m-Phenylendiamine. Derartige Substituenten sind beispielsweise Chlor, Brom, Methoxy, Ethoxy, Methyl, Ethyl, Nitro und Sulfonamido.In addition to the unsubstituted m-phenylenediamine, m-phenylenediamines substituted by conventional substituents are also suitable as starting products. Such substituents are, for example, chlorine, bromine, methoxy, ethoxy, methyl, ethyl, nitro and sulfonamido.
54 g (0,5 Mol) m-Phenyldiamin, 136 g (1 Mol) 60%ige wäßrige Glykolsäure und 60 g 30%ige Salzsäure werden 3 Stunden auf 105° erhitzt. Nach Zugabe von 600 ml Wasser werden 160 g Natriumchlorid zugesetzt, dann läßt man den Ansatz auf Raumtemperatur abkühlen. Das auskristallisierte Produkt wird isoliert und zweimal mit je 100 ml gesättigter Kochsalzlösung gewaschen und getrocknet.
Ausbeute: 45 g.54 g (0.5 mol) of m-phenyldiamine, 136 g (1 mol) of 60% aqueous glycolic acid and 60 g of 30% hydrochloric acid are heated to 105° for 3 hours. After adding 600 ml of water, 160 g of sodium chloride are added and the mixture is allowed to cool to room temperature. The crystallized product is isolated and washed twice with 100 ml of saturated sodium chloride solution and dried.
Yield: 45 g.
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803033003 DE3033003C2 (en) | 1980-09-02 | 1980-09-02 | Process for the preparation of optionally nucleus-substituted N-(3-aminophenyl)glycolic acid amides |
| CH562481A CH649281A5 (en) | 1980-09-02 | 1981-09-01 | Process for preparing optionally ring-substituted N-(3-aminophenyl)glycolamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803033003 DE3033003C2 (en) | 1980-09-02 | 1980-09-02 | Process for the preparation of optionally nucleus-substituted N-(3-aminophenyl)glycolic acid amides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3033003A1 DE3033003A1 (en) | 1982-04-01 |
| DE3033003C2 true DE3033003C2 (en) | 1987-03-12 |
Family
ID=6110944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803033003 Expired DE3033003C2 (en) | 1980-09-02 | 1980-09-02 | Process for the preparation of optionally nucleus-substituted N-(3-aminophenyl)glycolic acid amides |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH649281A5 (en) |
| DE (1) | DE3033003C2 (en) |
-
1980
- 1980-09-02 DE DE19803033003 patent/DE3033003C2/en not_active Expired
-
1981
- 1981-09-01 CH CH562481A patent/CH649281A5/en not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| CH649281A5 (en) | 1985-05-15 |
| DE3033003A1 (en) | 1982-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |