FR2476070A1 - Preparation d'amino-2 nitro-5 benzophenone et de ses derives halogeno-2' - Google Patents
Preparation d'amino-2 nitro-5 benzophenone et de ses derives halogeno-2' Download PDFInfo
- Publication number
- FR2476070A1 FR2476070A1 FR8003266A FR8003266A FR2476070A1 FR 2476070 A1 FR2476070 A1 FR 2476070A1 FR 8003266 A FR8003266 A FR 8003266A FR 8003266 A FR8003266 A FR 8003266A FR 2476070 A1 FR2476070 A1 FR 2476070A1
- Authority
- FR
- France
- Prior art keywords
- nitro
- amino
- general formula
- benzophenone
- benzoyl
- 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.)
- Granted
Links
- -1 nitro benzanilide Chemical compound 0.000 title claims description 9
- 238000006243 chemical reaction Methods 0.000 title description 4
- 230000007062 hydrolysis Effects 0.000 title description 2
- 238000006460 hydrolysis reaction Methods 0.000 title description 2
- UJHSIDUUJPTLDY-UHFFFAOYSA-N (2-nitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 UJHSIDUUJPTLDY-UHFFFAOYSA-N 0.000 title 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 16
- 150000002367 halogens Chemical group 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 238000005903 acid hydrolysis reaction Methods 0.000 claims abstract description 4
- KCBREZOWOLOPLW-UHFFFAOYSA-N 4-nitro-n-phenylbenzamide Chemical class C1=CC([N+](=O)[O-])=CC=C1C(=O)NC1=CC=CC=C1 KCBREZOWOLOPLW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical group [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- PZPZDEIASIKHPY-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-phenylmethanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 PZPZDEIASIKHPY-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims description 2
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract description 3
- 239000012965 benzophenone Substances 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical class C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 0 *c1ccccc1C(c(cc(cc1)[N+]([O-])=O)c1N)=O Chemical compound *c1ccccc1C(c(cc(cc1)[N+]([O-])=O)c1N)=O 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HKFKBQGYOFOVFH-UHFFFAOYSA-N 2-chloro-4-nitro-n-phenylbenzamide Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1C(=O)NC1=CC=CC=C1 HKFKBQGYOFOVFH-UHFFFAOYSA-N 0.000 description 1
- BYLPNCMTNANHEY-UHFFFAOYSA-N 2-fluoro-n-(4-nitrophenyl)benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)C1=CC=CC=C1F BYLPNCMTNANHEY-UHFFFAOYSA-N 0.000 description 1
- SDWAACKJISOIGZ-UHFFFAOYSA-N 7-chloro-1-methyl-5-phenyl-3h-1,4-benzodiazepin-2-one;2,2,2-trichloroethane-1,1-diol Chemical compound OC(O)C(Cl)(Cl)Cl.N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SDWAACKJISOIGZ-UHFFFAOYSA-N 0.000 description 1
- ZTEHQPVGEHUXHI-UHFFFAOYSA-N Nc(ccc([N+]([O-])=O)c1)c1C(c(cccc1)c1F)=O Chemical compound Nc(ccc([N+]([O-])=O)c1)c1C(c(cccc1)c1F)=O ZTEHQPVGEHUXHI-UHFFFAOYSA-N 0.000 description 1
- PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960002200 flunitrazepam Drugs 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- GMGQGZYFQSCZCW-UHFFFAOYSA-N n-(4-nitrophenyl)benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)C1=CC=CC=C1 GMGQGZYFQSCZCW-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 description 1
- 229960001454 nitrazepam Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8003266A FR2476070A1 (fr) | 1980-02-14 | 1980-02-14 | Preparation d'amino-2 nitro-5 benzophenone et de ses derives halogeno-2' |
| IT47772/81A IT1170707B (it) | 1980-02-14 | 1981-02-12 | Procedimento per preparare 2-ammino 5-nitro-benzofenone e suoi 2-alogeno-derivati |
| ES500078A ES500078A0 (es) | 1980-02-14 | 1981-02-14 | Procedimiento de preparar amino-2 nitro-5 benzofenona y sus derivados |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8003266A FR2476070A1 (fr) | 1980-02-14 | 1980-02-14 | Preparation d'amino-2 nitro-5 benzophenone et de ses derives halogeno-2' |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2476070A1 true FR2476070A1 (fr) | 1981-08-21 |
| FR2476070B1 FR2476070B1 (enExample) | 1983-12-09 |
Family
ID=9238582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8003266A Granted FR2476070A1 (fr) | 1980-02-14 | 1980-02-14 | Preparation d'amino-2 nitro-5 benzophenone et de ses derives halogeno-2' |
Country Status (3)
| Country | Link |
|---|---|
| ES (1) | ES500078A0 (enExample) |
| FR (1) | FR2476070A1 (enExample) |
| IT (1) | IT1170707B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103613548A (zh) * | 2013-12-10 | 2014-03-05 | 沈阳药科大学 | 富马酸尼唑苯酮的合成工艺 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD74798A (enExample) * | ||||
| DE1593967B1 (de) * | 1966-02-22 | 1972-05-31 | Richter Gedeon Vegyeszet | Verfahren zur Herstellung von substituierten 2-Amino-benzophenonen |
-
1980
- 1980-02-14 FR FR8003266A patent/FR2476070A1/fr active Granted
-
1981
- 1981-02-12 IT IT47772/81A patent/IT1170707B/it active
- 1981-02-14 ES ES500078A patent/ES500078A0/es active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD74798A (enExample) * | ||||
| DE1593967B1 (de) * | 1966-02-22 | 1972-05-31 | Richter Gedeon Vegyeszet | Verfahren zur Herstellung von substituierten 2-Amino-benzophenonen |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103613548A (zh) * | 2013-12-10 | 2014-03-05 | 沈阳药科大学 | 富马酸尼唑苯酮的合成工艺 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8201126A1 (es) | 1981-12-16 |
| IT8147772A1 (it) | 1982-08-12 |
| IT8147772A0 (it) | 1981-02-12 |
| FR2476070B1 (enExample) | 1983-12-09 |
| ES500078A0 (es) | 1981-12-16 |
| IT1170707B (it) | 1987-06-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |