IL27356A - Process for preparing 2-alkanoyl-4-halo-5-alkanoylaminophenols - Google Patents
Process for preparing 2-alkanoyl-4-halo-5-alkanoylaminophenolsInfo
- Publication number
- IL27356A IL27356A IL27356A IL2735667A IL27356A IL 27356 A IL27356 A IL 27356A IL 27356 A IL27356 A IL 27356A IL 2735667 A IL2735667 A IL 2735667A IL 27356 A IL27356 A IL 27356A
- Authority
- IL
- Israel
- Prior art keywords
- alkanoyl
- preparing
- alkanoylaminophenols
- halo
- general
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 zinc aluminum chloride iron chloride tin chloride aluminum bromide bismuth chloride titanium chloride antimony Chemical compound 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005618 Fries rearrangement reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Laminated Bodies (AREA)
Description
S Process for preparing la This invention provides a process for the tion of new of the general formula in whi group and is a halogen The novel compounds of formula I above are described and claimed in our copending Patent Application The process according to the present invention alkanolamino comprises heating a derivative of the general in which Rg and X have the same meaning as in formula I in presence of a catalyst to effect a Fries rearrangement of the compound of formula II to the corresponding compound of formula In formulae I and II the alkanoyl group may for butyryl or As alkanoyl the group there may be exemplified a residue of phatic acid such as 2735 Examples of the halogen atom X include chlorine As the in the process according to the there may be used the one usually employed for the Fried rearrangement such as zinc aluminum chloride iron chloride tin chloride aluminum bromide bismuth chloride titanium chloride antimony hydrogen hydrogen boron trifluoride or phosphorus pentachloride The present reaction can proceed without any but there may be employed a solvent inert to the reaction such as carbon disulfide carbon tetrachloride nitrobenzene benzene or alkanoyl The thus obtained phenols are novel and useful as intermediates for the production of pharmaceuticals having marked pharmacological activities such as narcotic and for e The following example is shown for illustration of this Example 1 To a suspension of 22 g of anhydrous aluminum chloride in 20 ml of carbon there are added 25 g of acetate and the resulting mixture is heated in an oil After the carbon fide is removed by the resulting mixture is heated at for 4 After the reaction is the reaction mixture is mixed with 10 aqueous solution of hydrochloric acid and extracted with ethyl The extract is washed with dried and concentrated to give 0 g of acetophenone as white crystals melting at 207 to for 6 insufficientOCRQuality
Claims (1)
1. CLAIMS Process for preparing phenols which is characterized by heating a halophenol derivative of the general wherein is an alkanoyl is an alkanoyl group and X is a halogen atom in the Presence of a catalyst to effect the rearrangement and obtaining a alkanoylaminophenol of the general wherein have each the same significance as designated For the Applicants ARTNERS insufficientOCRQuality
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP689066 | 1966-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27356A true IL27356A (en) | 1971-10-20 |
Family
ID=11650810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL27356A IL27356A (en) | 1966-02-05 | 1967-01-30 | Process for preparing 2-alkanoyl-4-halo-5-alkanoylaminophenols |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE693440A (en) |
| CH (1) | CH462199A (en) |
| ES (1) | ES336988A1 (en) |
| FI (1) | FI48068C (en) |
| FR (1) | FR1510345A (en) |
| GB (1) | GB1140013A (en) |
| GR (1) | GR32433B (en) |
| IL (1) | IL27356A (en) |
| NO (1) | NO132957C (en) |
| OA (1) | OA02691A (en) |
| SE (1) | SE352073B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4731480A (en) * | 1985-07-29 | 1988-03-15 | Ortho Pharmaceutical Corporation | Process for preparing 2-acyl-3,4-dialkoxyanilines |
-
1967
- 1967-01-30 IL IL27356A patent/IL27356A/en unknown
- 1967-01-30 GR GR670132433A patent/GR32433B/en unknown
- 1967-01-31 OA OA52741A patent/OA02691A/en unknown
- 1967-01-31 BE BE693440D patent/BE693440A/xx not_active IP Right Cessation
- 1967-02-01 GB GB4830/67A patent/GB1140013A/en not_active Expired
- 1967-02-01 FI FI670293A patent/FI48068C/en active
- 1967-02-02 FR FR93525A patent/FR1510345A/en not_active Expired
- 1967-02-03 CH CH162267A patent/CH462199A/en unknown
- 1967-02-03 ES ES336988A patent/ES336988A1/en not_active Expired
- 1967-02-03 SE SE01548/67A patent/SE352073B/xx unknown
- 1967-02-04 NO NO166709A patent/NO132957C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI48068B (en) | 1974-02-28 |
| OA02691A (en) | 1970-12-15 |
| CH462199A (en) | 1968-09-15 |
| FI48068C (en) | 1974-06-10 |
| FR1510345A (en) | 1968-01-19 |
| ES336988A1 (en) | 1968-01-16 |
| GB1140013A (en) | 1969-01-15 |
| NO132957C (en) | 1976-02-11 |
| SE352073B (en) | 1972-12-18 |
| GR32433B (en) | 1967-07-04 |
| BE693440A (en) | 1967-07-31 |
| NO132957B (en) | 1975-11-03 |
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