GB997653A - N-aryl-isatoic anhydride derivatives - Google Patents
N-aryl-isatoic anhydride derivativesInfo
- Publication number
- GB997653A GB997653A GB3664663A GB3664663A GB997653A GB 997653 A GB997653 A GB 997653A GB 3664663 A GB3664663 A GB 3664663A GB 3664663 A GB3664663 A GB 3664663A GB 997653 A GB997653 A GB 997653A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- general formula
- prepared
- reaction
- dichloro
- 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
- 239000002253 acid Substances 0.000 abstract 11
- 238000006243 chemical reaction Methods 0.000 abstract 8
- -1 3-trifluoromethylphenyl Chemical group 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 abstract 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 3
- 230000003647 oxidation Effects 0.000 abstract 3
- 238000007254 oxidation reaction Methods 0.000 abstract 3
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000012286 potassium permanganate Substances 0.000 abstract 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 abstract 1
- NOHBAFVNPWPORE-UHFFFAOYSA-N 1,3-dichloro-4-methoxy-2-nitrobenzene Chemical compound COC1=CC=C(Cl)C([N+]([O-])=O)=C1Cl NOHBAFVNPWPORE-UHFFFAOYSA-N 0.000 abstract 1
- GLNRZGZHZYONRE-UHFFFAOYSA-N 2,4-dichloro-3-nitrophenol Chemical compound OC1=CC=C(Cl)C([N+]([O-])=O)=C1Cl GLNRZGZHZYONRE-UHFFFAOYSA-N 0.000 abstract 1
- HAIBRTRWRXXIDR-UHFFFAOYSA-N 2,6-dichloro-3-methoxyaniline Chemical compound COC1=CC=C(Cl)C(N)=C1Cl HAIBRTRWRXXIDR-UHFFFAOYSA-N 0.000 abstract 1
- ZIBSETYNBXBWFB-UHFFFAOYSA-N 2-(2,6-dichloro-3-methoxyanilino)benzoic acid Chemical compound COC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl ZIBSETYNBXBWFB-UHFFFAOYSA-N 0.000 abstract 1
- YVBKADMQQKJDRI-UHFFFAOYSA-N 2-(3-ethyl-2,6-dimethylanilino)benzoic acid Chemical compound CCC1=CC=C(C)C(NC=2C(=CC=CC=2)C(O)=O)=C1C YVBKADMQQKJDRI-UHFFFAOYSA-N 0.000 abstract 1
- PFEIMKNQOIFKSW-UHFFFAOYSA-N 2-chloro-4-methylquinoline Chemical compound C1=CC=C2C(C)=CC(Cl)=NC2=C1 PFEIMKNQOIFKSW-UHFFFAOYSA-N 0.000 abstract 1
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 abstract 1
- PPBJKIZZUGILIO-UHFFFAOYSA-N 3-ethyl-2,6-dimethylaniline Chemical compound CCC1=CC=C(C)C(N)=C1C PPBJKIZZUGILIO-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 229910001502 inorganic halide Inorganic materials 0.000 abstract 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- NRPTXWYBRKRZES-UHFFFAOYSA-N n-(2,6-dimethylphenyl)acetamide Chemical compound CC(=O)NC1=C(C)C=CC=C1C NRPTXWYBRKRZES-UHFFFAOYSA-N 0.000 abstract 1
- 150000004967 organic peroxy acids Chemical class 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22452062A | 1962-09-18 | 1962-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB997653A true GB997653A (en) | 1965-07-07 |
Family
ID=22841052
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3664663A Expired GB997653A (en) | 1962-09-18 | 1963-09-17 | N-aryl-isatoic anhydride derivatives |
| GB3664863A Expired GB1001356A (en) | 1962-09-18 | 1963-09-17 | Substituted anthranilic acid esters |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3664863A Expired GB1001356A (en) | 1962-09-18 | 1963-09-17 | Substituted anthranilic acid esters |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE637515A (OSRAM) |
| BR (1) | BR6352807D0 (OSRAM) |
| CH (4) | CH416630A (OSRAM) |
| DE (1) | DE1470212A1 (OSRAM) |
| ES (1) | ES291742A1 (OSRAM) |
| FR (1) | FR2935M (OSRAM) |
| GB (2) | GB997653A (OSRAM) |
| NL (2) | NL123926C (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2572072B1 (fr) * | 1984-10-18 | 1989-04-14 | Basf Ag | Procede de preparation de derives d'indole |
-
0
- BE BE637515D patent/BE637515A/xx unknown
- NL NL298016D patent/NL298016A/xx unknown
- NL NL123926D patent/NL123926C/xx active
-
1963
- 1963-09-16 DE DE19631470212 patent/DE1470212A1/de active Pending
- 1963-09-17 CH CH673566A patent/CH416630A/fr unknown
- 1963-09-17 CH CH673766A patent/CH416632A/fr unknown
- 1963-09-17 CH CH673666A patent/CH416631A/fr unknown
- 1963-09-17 GB GB3664663A patent/GB997653A/en not_active Expired
- 1963-09-17 FR FR947774A patent/FR2935M/fr active Active
- 1963-09-17 ES ES291742A patent/ES291742A1/es not_active Expired
- 1963-09-17 GB GB3664863A patent/GB1001356A/en not_active Expired
- 1963-09-17 BR BR15280763A patent/BR6352807D0/pt unknown
- 1963-09-17 CH CH1147663A patent/CH415635A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES291742A1 (es) | 1964-02-16 |
| FR2935M (fr) | 1964-11-16 |
| DE1470212A1 (de) | 1969-04-24 |
| CH416631A (fr) | 1966-07-15 |
| CH415635A (fr) | 1966-06-30 |
| NL298016A (OSRAM) | |
| CH416630A (fr) | 1966-07-15 |
| BR6352807D0 (pt) | 1973-06-12 |
| NL123926C (OSRAM) | |
| GB1001356A (en) | 1965-08-18 |
| CH416632A (fr) | 1966-07-15 |
| BE637515A (OSRAM) |
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