GB1028920A - Production of di-aryl-substituted-benzenes - Google Patents
Production of di-aryl-substituted-benzenesInfo
- Publication number
- GB1028920A GB1028920A GB4555363A GB4555363A GB1028920A GB 1028920 A GB1028920 A GB 1028920A GB 4555363 A GB4555363 A GB 4555363A GB 4555363 A GB4555363 A GB 4555363A GB 1028920 A GB1028920 A GB 1028920A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isoindole
- substituted
- formula
- acid
- tetraphenyl
- 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
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkali metal nitrite Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- YBHPWRGGYIDPLJ-UHFFFAOYSA-N 1,3,4,7-tetraphenyl-2H-isoindole Chemical compound C1(=CC=CC=C1)C=1NC(=C2C(=CC=C(C12)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 YBHPWRGGYIDPLJ-UHFFFAOYSA-N 0.000 abstract 1
- BCYMBQICGHGBGM-UHFFFAOYSA-N C1=CC=CC=C1C1=CC=C(C(=NN=C2C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C1C1=CC=CC=C1 Chemical compound C1=CC=CC=C1C1=CC=C(C(=NN=C2C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C1C1=CC=CC=C1 BCYMBQICGHGBGM-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 235000010288 sodium nitrite Nutrition 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process of producing di-aroyl-substituted benzenes having the general formula <FORM:1028920/C2/1> wherein A1 and A2 are the same or different and each is an unsubstituted or substituted phenyl or other aryl group, R1 and R2 are the same or different and each is an alkyl, or aryl group, comprises contacting the corresponding isoindole having the formula <FORM:1028920/C2/2> wherein the groups A1, A2, R1 and R2 have the previous significance with nitrous acid or with reactants capable of producing nitrous acid under the conditions of the reaction, e.g. with a mixture of alkali metal nitrite and an inorganic or organic acid. The isoindole used as starting material is obtained by reacting the corresponding 2,5-di-substituted pyrrole having the general formula <FORM:1028920/C2/3> with the gamma-diketone having the formula R2.CO.CH2CH2CO.R1 wherein the groups A1, A2, R1 and R2 are as above. In an example 2,3-di-benzoyl-1 : 4-diphenyl benzene is produced by adding sodium nitrite to a solution of 1,3,4,7-tetraphenyl isoindole in a mixture of glacial acetic acid and hydrochloric acid and re-crystallizing the separated product. Reaction of the latter with hydrazine hydrate produced 1458 tetraphenyl phthalazine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4555363A GB1028920A (en) | 1963-11-19 | 1963-11-19 | Production of di-aryl-substituted-benzenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4555363A GB1028920A (en) | 1963-11-19 | 1963-11-19 | Production of di-aryl-substituted-benzenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1028920A true GB1028920A (en) | 1966-05-11 |
Family
ID=10437638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4555363A Expired GB1028920A (en) | 1963-11-19 | 1963-11-19 | Production of di-aryl-substituted-benzenes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1028920A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8338591B2 (en) * | 2004-05-08 | 2012-12-25 | Novartis International Pharmaceutical Ltd. | 3-aryl-5,6-disubstituted pyridazines |
-
1963
- 1963-11-19 GB GB4555363A patent/GB1028920A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8338591B2 (en) * | 2004-05-08 | 2012-12-25 | Novartis International Pharmaceutical Ltd. | 3-aryl-5,6-disubstituted pyridazines |
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