GB593655A - Process of preparing acylamino dianthrimide acridones - Google Patents
Process of preparing acylamino dianthrimide acridonesInfo
- Publication number
- GB593655A GB593655A GB1549345A GB1549345A GB593655A GB 593655 A GB593655 A GB 593655A GB 1549345 A GB1549345 A GB 1549345A GB 1549345 A GB1549345 A GB 1549345A GB 593655 A GB593655 A GB 593655A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dianthrimide
- benzoylamino
- acid
- carboxylic acid
- acridones
- 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
- -1 acylamino dianthrimide acridones Chemical class 0.000 title 1
- SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 abstract 4
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 3
- 235000011149 sulphuric acid Nutrition 0.000 abstract 3
- 239000001117 sulphuric acid Substances 0.000 abstract 3
- WITKIIIPSSFHST-UHFFFAOYSA-N 1-[(9,10-dioxoanthracen-1-yl)amino]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC1=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=C1 WITKIIIPSSFHST-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000004442 acylamino group Chemical group 0.000 abstract 2
- 230000001476 alcoholic Effects 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000004702 methyl esters Chemical class 0.000 abstract 2
- 229940072033 potash Drugs 0.000 abstract 2
- 235000015320 potassium carbonate Nutrition 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 2
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- FWEQPMZEKHHFTB-UHFFFAOYSA-N N-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 abstract 1
- LRZQPQJEYDUCKH-UHFFFAOYSA-N N-(6-chloro-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1NC(=O)C1=CC=CC=C1 LRZQPQJEYDUCKH-UHFFFAOYSA-N 0.000 abstract 1
- 210000004940 Nucleus Anatomy 0.000 abstract 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical class ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- INZRQUGQPAEYFR-UHFFFAOYSA-N benzyl 1-chloro-9,10-dioxoanthracene-2-carboxylate Chemical compound C1=CC=2C(=O)C3=CC=CC=C3C(=O)C=2C(Cl)=C1C(=O)OCC1=CC=CC=C1 INZRQUGQPAEYFR-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing Effects 0.000 abstract 1
- QIAAPANEUUVUSA-UHFFFAOYSA-N methyl 1-amino-9,10-dioxoanthracene-2-carboxylate Chemical compound C1=CC=C2C(=O)C3=C(N)C(C(=O)OC)=CC=C3C(=O)C2=C1 QIAAPANEUUVUSA-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1.11-Dianthrimide-2.21-acridones and 2.11-dianthrimide-1.21-acridones having an acylamino group in an alpha-position of a terminal nucleus are prepared by subjecting the appropriate ortho-carboxy monoacylamino dianthrimide or its ester to ring closure in the presence of a condensing agent having no hydrolytic action on the acylamino group, and preferably in an organic solvent. Condensing agents specified are benzoyl, acetyl and thionyl chlorides, acetic anhydride and phosphorus oxychloride, and these are preferably employed with not more than 25 per cent of sulphuric acid, based on the weight of dianthrimide. The products may be purified by recrystallization from nitrobenzene, fractional precipitation of the sulphates from sulphuric acid, acid-pasting, or vatting. In examples, the following substances are heated with benzoyl chloride in nitrobenzene in presence of a little sulphuric acid: (1) 5-benzoylamino-1.11-dianthrimide-21-carboxylic acid and its benzyl ester; (2) 5-benzoylamino-2.11-dianthrimide-21-carboxylic acid. 5-Benzoylamino-1.1-dianthrimide-21-carboxylic acid and its benzyl ester are prepared by reacting 1 - benzoylamino - 5 - aminoanthraquinone with 1-chloranthraquinone-2-carboxylic acid benzyl ester, the benzyl ester so obtained being hydrolysed to the acid with alcoholic potash. 5 - Benzoylamino - 2.11 - dianthrimide - 21 - carboxylic acid and its methyl ester are made by reacting 1-benzoylamino-6-chloranthraquinone with 1-aminoanthraquinone-2-carboxylic acid methyl ester, the methyl ester so obtained being hydrolysed to the acid with alcoholic potash. Specification 291,878, [Class 2 (iii)], is referred to.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB593655A true GB593655A (en) | 1947-10-22 |
Family
ID=1731557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1549345A Expired GB593655A (en) | 1945-06-18 | Process of preparing acylamino dianthrimide acridones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB593655A (en) |
-
1945
- 1945-06-18 GB GB1549345A patent/GB593655A/en not_active Expired
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