GB723946A - Improvements in and relating to derivatives of 3-(4-hydroxyphenyl)-3-(4-hydroxy-methyl-phenyl)-oxindole - Google Patents
Improvements in and relating to derivatives of 3-(4-hydroxyphenyl)-3-(4-hydroxy-methyl-phenyl)-oxindoleInfo
- Publication number
- GB723946A GB723946A GB23426/52A GB2342652A GB723946A GB 723946 A GB723946 A GB 723946A GB 23426/52 A GB23426/52 A GB 23426/52A GB 2342652 A GB2342652 A GB 2342652A GB 723946 A GB723946 A GB 723946A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxyphenyl
- oxindole
- acid
- amide
- butoxy
- 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
- JJFPLGYKQXOJGU-UHFFFAOYSA-N 3-(4-hydroxy-2-methylphenyl)-3-(4-hydroxyphenyl)-1H-indol-2-one Chemical class OC1=CC=C(C=C1)C1(C(NC2=CC=CC=C12)=O)C1=C(C=C(C=C1)O)C JJFPLGYKQXOJGU-UHFFFAOYSA-N 0.000 title 1
- -1 alkyl radical Chemical class 0.000 abstract 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 abstract 3
- 150000001408 amides Chemical class 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
Classifications
-
- 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
- C07D209/34—Oxygen atoms in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises derivatives of 3-(41-hydroxyphenyl) - 3 - (311 - aminomethyl - 411 - hydroxyphenyl)-oxindole of the general formula <FORM:0723946/IV (b)/1> wherein R1 represents hydrogen or the acetyl group, R2 represents an alkyl radical containing from 2 to 6 carbon atoms or the cyclohexyl radical and R3 represents hydrogen or an alkyl radical with at most 2 carbon atoms. Such compounds are obtained by condensing a compound of the formula <FORM:0723946/IV (b)/2> with an N-hydroxymethyl amide of the general formula HO-CH2-NH-COCH(R3)-OR2 and if desired, acetylating those condensation products with a free hydroxyl group OR1. Zinc chloride in glacial acetic acid, concentrated sulphuric acid or alcoholic hydrochloric acid may be used as condensing agents. In example (1) 3 : 3 - bis - (41 - hydroxyphenyl) - oxindole and N-hydroxymethyl-n-butoxy acetamide are reacted to give 3-(41-hydroxyphenyl)-3-(311-n-butoxy acetylamino methyl - 411 - hydroxy - phenyl)-oxindole which on reaction with acetic anhydride gives the corresponding di-acetoxy derivative. Similarly prepared are (2) 3-(41-hydroxyphenyl) - 3 - (311 - cyclohexyloxy - acetaminomethyl - 411 - hydroxyphenyl) - oxindole and its di-acetyl derivative; (3) 3-(41-hydroxyphenyl) - 3 - [311 - (a - n - butoxypro - pionylaminomethyl) - 411 - hydroxyphenyl] - oxindole; (4) 3 - (41 - hydroxyphenyl) - [311 - (a - ethoxybutyrylamino - methyl) - 411 - hydroxy - phenyl]-oxindole. Similarly obtained are 3-(41-hydroxyphenyl) - 3 - (311 - acylaminomethyl - 411 - hydroxyphenyl) - oxindoles in which the acyl radicals are n - propoxyacetyl, iso - butoxyacetyl, isoamyloxyacetyl, n - hexyloxy - acetyl, a - ethoxypropionyl, a - n - propoxypro - pionyl, a - isoamyl - oxypropionyl, a - n - pro - poxybutyryl, a - n - butoxy - butyryl and a - isoamyloxybutyryl radicals respectively. The N-hydroxymethylamides are obtained by reacting aqueous formaldehyde with the corresponding a -alkoxy fatty acid amides. N-Hydroxymethyl - a - n - butoxy - propionic acid amide is obtained by reacting n-butanol with a -bromopropionic acid to give a -n-butoxypropionic acid which is converted to its amide via the acid chloride, the amide then being reacted with aqueous formaldehyde. The amide can also be prepared by reacting a -chlorethylbutyl ether with cuprous cyanide and hydrolysing the nitrile produced. N-Hydroxymethyl-a -ethoxy-butyric acid amide is produced from a - ethoxybutyric acid amide, obtained analagously to a -n-butoxy-propionic acid amide or from a -ethoxy butyric acid ethyl ester and alcoholic ammonia.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH723946X | 1951-09-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB723946A true GB723946A (en) | 1955-02-16 |
Family
ID=4531757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23426/52A Expired GB723946A (en) | 1951-09-21 | 1952-09-18 | Improvements in and relating to derivatives of 3-(4-hydroxyphenyl)-3-(4-hydroxy-methyl-phenyl)-oxindole |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB723946A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006003210A1 (en) * | 2004-07-07 | 2006-01-12 | Symrise Gmbh & Co. Kg | Use of alkyloxyalcanic acid amides, in particular in the form of aromatic substances and a novel alkyloxyalcanic acid amide |
-
1952
- 1952-09-18 GB GB23426/52A patent/GB723946A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006003210A1 (en) * | 2004-07-07 | 2006-01-12 | Symrise Gmbh & Co. Kg | Use of alkyloxyalcanic acid amides, in particular in the form of aromatic substances and a novel alkyloxyalcanic acid amide |
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