CH310148A - Process for the preparation of a substantive 2,3-oxynaphthoic acid arylide. - Google Patents
Process for the preparation of a substantive 2,3-oxynaphthoic acid arylide.Info
- Publication number
- CH310148A CH310148A CH310148DA CH310148A CH 310148 A CH310148 A CH 310148A CH 310148D A CH310148D A CH 310148DA CH 310148 A CH310148 A CH 310148A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- substantive
- oxynaphthoic acid
- acid arylide
- arylide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
- C09B43/132—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters having the carboxylic group directly attached to an aromatic carbocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 305720. Verfahren zur Herstellung eines Substantiven 2,3-Oxynaphthoesäurearylids. (legenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Herstellung eines Substantiven 2,3 - Oxynaphthoesäurearylids, welches dadurch gekennzeichnet ist, dass man 2,3-Oxynaphthoesäitre oder eines ihrer funk- tionellen Derivate mit 1-(3'-Aminophenyl)-3- nietliyl-4-(naphthalin-1"-azo)-5-pyrazolon kon densiert.
Die erhaltene, bisher nicht bekannte Ver bindung stellt ein wertvolles Zwischenprodukt für die Herstellung von Azofarbstoffen dar. <I>Beispiel:</I> 34 Gewichtsteile gut getrocknetes 1-(3'- Aminophenyl) - 3-methyl-4-naphthalin-1"-azo) - 5-pyrazolon von der folgenden Formel
EMI0001.0015
(e rhältlieh dureh Kuppeln von diazotiertem 1-Amino-naphthalin mit 1-(3'-Aminophenyl)- :
i-methyl-5-pyrazolon) werden in 400 Ge- wielltsteilen wasserfreiem Toluol verrührt und auf 100 C erhitzt. Bei dieser Temperatur lässt man innerhalb einiger Minuten eine Lö sung von 2,3-Oxynaphthoesäiirechlorid, das durch mehrstündiges Erhitzen von 19 Ge- wiehtsteilen 2,3-Oxynaphthoesäure in 200 Ge- wiclitsteilen wasserfreiem Toluol unter Zu tropfen von 1.1 Gewichtsteilen Thionylchlorid auf 85--90 C hergestellt wurde,
zulaufen. Man erhitzt 4 Stunden zum Sieden, saugt dann heiss ab, wäscht mit etwas Toluol und anschliessend mit Methanol nach. Zur Ent fernung geringer Mengen 2,3-Oxynaphthoe- säure kocht. man den Rückstand mit verdünn ter Sodalösung aus. Das erhaltene Arylid stellt nach dem Trocknen ein gelbbraunes Pulver dar, das bei 226 C schmilzt.
<B> Additional patent </B> to main patent no. 305720. Process for the preparation of a noun 2,3-oxynaphthoic acid arylide. (The status of the present additional patent is a process for the production of a noun 2,3 - Oxynaphthoesäurearylids, which is characterized in that 2,3-Oxynaphthoesäitre or one of its functional derivatives with 1- (3'-aminophenyl) -3- nietliyl-4- (naphthalene-1 "-azo) -5-pyrazolone condensed.
The compound obtained, previously unknown, represents a valuable intermediate product for the production of azo dyes. <I> Example: </I> 34 parts by weight of well-dried 1- (3'-aminophenyl) -3-methyl-4-naphthalene-1 "-azo) - 5-pyrazolone of the following formula
EMI0001.0015
(Obtained by coupling diazotized 1-amino-naphthalene with 1- (3'-aminophenyl) -:
i-methyl-5-pyrazolone) are stirred in 400 parts by weight of anhydrous toluene and heated to 100.degree. At this temperature, a solution of 2,3-oxynaphthoic acid chloride is left within a few minutes, which is obtained by heating 19 parts by weight of 2,3-oxynaphthoic acid in 200 parts by weight of anhydrous toluene for several hours, adding 1.1 parts by weight of thionyl chloride to 85-- 90 C was made,
run towards. The mixture is heated to boiling for 4 hours, then filtered off with suction while hot, washed with a little toluene and then with methanol. To remove small amounts of 2,3-oxynaphthoic acid, boils. the residue is extracted with dilute soda solution. The arylide obtained is a yellow-brown powder which melts at 226 ° C. after drying.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE310148X | 1951-05-26 | ||
| CH305720T | 1952-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH310148A true CH310148A (en) | 1955-09-30 |
Family
ID=25734993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310148D CH310148A (en) | 1951-05-26 | 1952-05-24 | Process for the preparation of a substantive 2,3-oxynaphthoic acid arylide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH310148A (en) |
-
1952
- 1952-05-24 CH CH310148D patent/CH310148A/en unknown
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