CA1062728A - Process for the preparation of 2-(4-isobutylphenyl)-propiohydroxamic acid - Google Patents
Process for the preparation of 2-(4-isobutylphenyl)-propiohydroxamic acidInfo
- Publication number
- CA1062728A CA1062728A CA237,341A CA237341A CA1062728A CA 1062728 A CA1062728 A CA 1062728A CA 237341 A CA237341 A CA 237341A CA 1062728 A CA1062728 A CA 1062728A
- Authority
- CA
- Canada
- Prior art keywords
- methanol
- precipitate
- mixture
- isobutylphenyl
- reaction product
- 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
- 238000000034 method Methods 0.000 title claims abstract description 11
- BYPIURIATSUHDW-UHFFFAOYSA-N ibuproxam Chemical compound CC(C)CC1=CC=C(C(C)C(=O)NO)C=C1 BYPIURIATSUHDW-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 15
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 10
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000002244 precipitate Substances 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- PKQKHWNHCKNYSW-UHFFFAOYSA-N (+-)-2-(4'-isobutylphenyl)propionitrile Chemical compound CC(C)CC1=CC=C(C(C)C#N)C=C1 PKQKHWNHCKNYSW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 4
- 239000007858 starting material Substances 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 7
- 238000007865 diluting Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 230000001376 precipitating effect Effects 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 238000009738 saturating Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- 229940083608 sodium hydroxide Drugs 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 2
- XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000009740 moulding (composite fabrication) Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- -1 isobutylphenyl Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000005599 propionic acid derivatives Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT5440074A IT1046338B (it) | 1974-12-06 | 1974-12-06 | Procedimento per preparare aoido 2,4 isoputil fenil propioidros sanico e combusto intermerio beriesso |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1062728A true CA1062728A (en) | 1979-09-18 |
Family
ID=11287260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA237,341A Expired CA1062728A (en) | 1974-12-06 | 1975-10-09 | Process for the preparation of 2-(4-isobutylphenyl)-propiohydroxamic acid |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5168537A (OSRAM) |
| AT (1) | AT339881B (OSRAM) |
| BE (1) | BE830825R (OSRAM) |
| CA (1) | CA1062728A (OSRAM) |
| CH (1) | CH595318A5 (OSRAM) |
| DE (1) | DE2516267C2 (OSRAM) |
| DK (1) | DK155475A (OSRAM) |
| ES (1) | ES436706A1 (OSRAM) |
| FR (1) | FR2293423A2 (OSRAM) |
| GB (1) | GB1472012A (OSRAM) |
| IT (1) | IT1046338B (OSRAM) |
| NL (1) | NL161138C (OSRAM) |
| YU (1) | YU257775A (OSRAM) |
| ZA (1) | ZA752571B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792560A (en) * | 1985-04-03 | 1988-12-20 | Rorer Pharmaceutical Corporation | Quinoline hydroxamates and their use as modulators of arachidonic acid metabolic pathways |
-
1974
- 1974-12-06 IT IT5440074A patent/IT1046338B/it active
-
1975
- 1975-04-09 GB GB1449375A patent/GB1472012A/en not_active Expired
- 1975-04-10 DK DK155475A patent/DK155475A/da not_active IP Right Cessation
- 1975-04-14 DE DE19752516267 patent/DE2516267C2/de not_active Expired
- 1975-04-17 ES ES436706A patent/ES436706A1/es not_active Expired
- 1975-04-22 ZA ZA00752571A patent/ZA752571B/xx unknown
- 1975-05-27 JP JP6340675A patent/JPS5168537A/ja active Granted
- 1975-06-19 FR FR7519211A patent/FR2293423A2/fr active Granted
- 1975-06-30 BE BE157834A patent/BE830825R/xx not_active IP Right Cessation
- 1975-10-08 AT AT769475A patent/AT339881B/de not_active IP Right Cessation
- 1975-10-09 CA CA237,341A patent/CA1062728A/en not_active Expired
- 1975-10-09 YU YU257775A patent/YU257775A/xx unknown
- 1975-10-09 NL NL7511903A patent/NL161138C/xx active
- 1975-10-14 CH CH1332175A patent/CH595318A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2516267A1 (de) | 1976-06-10 |
| FR2293423A2 (fr) | 1976-07-02 |
| YU257775A (en) | 1982-05-31 |
| GB1472012A (en) | 1977-04-27 |
| ZA752571B (en) | 1976-05-26 |
| JPS5168537A (en) | 1976-06-14 |
| NL7511903A (nl) | 1976-06-09 |
| BE830825R (fr) | 1975-10-16 |
| FR2293423B2 (OSRAM) | 1977-07-22 |
| CH595318A5 (OSRAM) | 1978-02-15 |
| AT339881B (de) | 1977-11-10 |
| IT1046338B (it) | 1980-06-30 |
| JPS548668B2 (OSRAM) | 1979-04-17 |
| DK155475A (da) | 1976-06-07 |
| AU8563475A (en) | 1977-04-21 |
| ATA769475A (de) | 1977-03-15 |
| ES436706A1 (es) | 1977-01-16 |
| NL161138C (nl) | 1980-01-15 |
| DE2516267C2 (de) | 1982-07-01 |
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