GB898045A - Nuclearly substituted anilines and nitrobenzenes and their preparation - Google Patents
Nuclearly substituted anilines and nitrobenzenes and their preparationInfo
- Publication number
- GB898045A GB898045A GB1612959A GB1612959A GB898045A GB 898045 A GB898045 A GB 898045A GB 1612959 A GB1612959 A GB 1612959A GB 1612959 A GB1612959 A GB 1612959A GB 898045 A GB898045 A GB 898045A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- appropriate
- phenol
- reacting
- nitro
- 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
- 238000002360 preparation method Methods 0.000 title abstract 3
- 150000001448 anilines Chemical class 0.000 title 1
- 150000005181 nitrobenzenes Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 12
- -1 aminoalkyl halide Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001555 benzenes Chemical class 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 239000012954 diazonium Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 150000007522 mineralic acids Chemical class 0.000 abstract 2
- 230000000802 nitrating effect Effects 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 2
- XUIKECLBCZBUCM-UHFFFAOYSA-N 1,2-dipropoxybenzene Chemical compound CCCOC1=CC=CC=C1OCCC XUIKECLBCZBUCM-UHFFFAOYSA-N 0.000 abstract 1
- RYNFYPWJNRXYGG-UHFFFAOYSA-N 4-nitro-1,2-dipropoxybenzene Chemical compound CCCOC1=CC=C([N+]([O-])=O)C=C1OCCC RYNFYPWJNRXYGG-UHFFFAOYSA-N 0.000 abstract 1
- ZLIUCKSKAZKFLO-UHFFFAOYSA-N 4-nitro-2-propoxyphenol Chemical compound CCCOC1=CC([N+]([O-])=O)=CC=C1O ZLIUCKSKAZKFLO-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000010255 intramuscular injection Methods 0.000 abstract 1
- 238000010253 intravenous injection Methods 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- OCNPXKLQSGAGKT-UHFFFAOYSA-N propyl benzenesulfonate Chemical compound CCCOS(=O)(=O)C1=CC=CC=C1 OCNPXKLQSGAGKT-UHFFFAOYSA-N 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
- 239000005526 vasoconstrictor agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises substituted benzenes of the formula <FORM:0898045/IV (b)/1> (wherein R is a hydrocarbon radical of at most 8 carbon atoms, Z is NO2 or NHY, Y being hydrogen or alkanoyl of at most 6 carbon atoms, X is an alkylene radical of 2, 3 or 4 carbon atoms and has its valencies on different carbon atoms and NB is dialkylamino wherein each alkyl group contains at most 6 carbon atoms or piperidino or 1-pyrrolidinyl which may be substituted by alkyl radicals containing at most 4 carbon atoms) and their acid-addition salts; and their preparation by reacting an appropriate halo-(RO)-nitro-phenol with an appropriate tertiary aminoalkyl halide and when required reducing the nitro compound to an amino compound and, when required, acylating this. Alternatively an appropriate halo-alkyl halide can be used as the second reaction component and the product reacted with a tertiary amine. Examples are given and a list of saltforming organic and inorganic acids is provided. Compounds of the formula <FORM:0898045/IV (b)/2> wherein the halogen is chlorine, bromine or iodine are prepared (1) by halogenating an appropriate (RO)-nitro-phenol; or (2) by nitrating an appropriate (RO)-halo-phenol; or (3) by reacting an (RO)-halo-hydroxy-benzaldehyde with fuming nitric acid. When the halogen is fluorine they are prepared by diazotizing an (RO)-amino-nitro-phenol, reacting the diazonium salt with fluoboric acid to form the diazonium fluoborate and heating this. 2-n-Propoxy-4-nitrophenol is prepared by reacting catechol with n-propyl benzene sulphonate to form 1,2-di-n-propoxy-benzene, nitrating this to 1,2-di-n-propoxy-4-nitrobenzene and monodealkylating this. The corresponding methoxy, ethoxy, butoxy, hexoxy and benzyloxy compounds are prepared similarly.ALSO:Substituted benzenes of the formula <FORM:0898045/VI/1> (wherein R is a hydrocarbon radical of at most 8 carbon atoms, Z is NO2 or NHY, Y being hydrogen or alkanoyl of at most 6 carbon atoms, X is an alkylene radical of 2, 3 or 4 carbon atoms and has its valencies on different carbon atoms and NB is dialkylamino wherein each alkyl group contains at most 6 carbon atoms or piperidino or 1-pyrrolidinyl which may be substituted by alkyl radicals containing at most 4 carbon atoms) or salts thereof with organic or inorganic acids, may be formulated as local anaesthetic compositions. Conveniently, the salts are used in aqueous preparations for topical administration or intramuscular or intravenous injection. The active compounds may advantageously be combined with other pharmacologically active compounds, e.g. vasoconstrictor agents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1612959A GB898045A (en) | 1959-05-11 | 1959-05-11 | Nuclearly substituted anilines and nitrobenzenes and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1612959A GB898045A (en) | 1959-05-11 | 1959-05-11 | Nuclearly substituted anilines and nitrobenzenes and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB898045A true GB898045A (en) | 1962-06-06 |
Family
ID=10071705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1612959A Expired GB898045A (en) | 1959-05-11 | 1959-05-11 | Nuclearly substituted anilines and nitrobenzenes and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB898045A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0926119A1 (en) * | 1997-12-10 | 1999-06-30 | Union Carbide Chemicals & Plastics Technology Corporation | Dialkoxybenzene electron donors |
-
1959
- 1959-05-11 GB GB1612959A patent/GB898045A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0926119A1 (en) * | 1997-12-10 | 1999-06-30 | Union Carbide Chemicals & Plastics Technology Corporation | Dialkoxybenzene electron donors |
| US6124507A (en) * | 1997-12-10 | 2000-09-26 | Union Carbide Chemicals & Plastics Technology Corporation | Electron donors |
| US6399837B1 (en) | 1997-12-10 | 2002-06-04 | Union Carbide Chemicals & Plastics Technology Corporation | Electron donors |
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