DE1793040A1 - Verfahren zur Herstellung von 1-(3,5-Dimethoxy-4-hydroxyphenyl)-2-monomethylaminoaethanol - Google Patents
Verfahren zur Herstellung von 1-(3,5-Dimethoxy-4-hydroxyphenyl)-2-monomethylaminoaethanolInfo
- Publication number
- DE1793040A1 DE1793040A1 DE19681793040 DE1793040A DE1793040A1 DE 1793040 A1 DE1793040 A1 DE 1793040A1 DE 19681793040 DE19681793040 DE 19681793040 DE 1793040 A DE1793040 A DE 1793040A DE 1793040 A1 DE1793040 A1 DE 1793040A1
- Authority
- DE
- Germany
- Prior art keywords
- dimethoxy
- hydroxy
- acetoxy
- hydroxyphenyl
- preparation
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 4
- ZKGDBJAHIIXDDW-UHFFFAOYSA-N dimetofrine Chemical compound CNCC(O)C1=CC(OC)=C(O)C(OC)=C1 ZKGDBJAHIIXDDW-UHFFFAOYSA-N 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 2
- LNBMZFHIYRDKNS-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylethanone Chemical compound COC(OC)C(=O)C1=CC=CC=C1 LNBMZFHIYRDKNS-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 dimethoxy-4-hydroxyphenyl Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 1
- SUFHOFZQYXKUCA-UHFFFAOYSA-N acetosyringone acetate Chemical compound COC1=CC(C(C)=O)=CC(OC)=C1OC(C)=O SUFHOFZQYXKUCA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1545568A IT1143626B (it) | 1968-04-18 | 1968-04-18 | Processo per la fabbricazione di (13,5 dimetossi 4 idrossi) 2 monometilamminoetanolo,farmaco ad azione ipertensiva |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1793040A1 true DE1793040A1 (de) | 1972-08-03 |
Family
ID=11148022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681793040 Pending DE1793040A1 (de) | 1968-04-18 | 1968-07-26 | Verfahren zur Herstellung von 1-(3,5-Dimethoxy-4-hydroxyphenyl)-2-monomethylaminoaethanol |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE718518A (en)) |
| CH (1) | CH512431A (en)) |
| DE (1) | DE1793040A1 (en)) |
| DK (1) | DK127638B (en)) |
| ES (1) | ES355063A2 (en)) |
| FR (1) | FR1585414A (en)) |
| GB (1) | GB1188480A (en)) |
| IT (1) | IT1143626B (en)) |
| SE (1) | SE354852B (en)) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1044224B (it) * | 1972-09-07 | 1980-03-20 | Zambeletti Spa L | 2 idrossi 2 feniletilamine sostituite quali sostanze vasoattive e processo per la loro preparazione |
-
1968
- 1968-04-18 IT IT1545568A patent/IT1143626B/it active
- 1968-06-15 ES ES355063A patent/ES355063A2/es not_active Expired
- 1968-06-20 DK DK293868A patent/DK127638B/da not_active IP Right Cessation
- 1968-06-20 SE SE845768A patent/SE354852B/xx unknown
- 1968-06-20 GB GB2956868A patent/GB1188480A/en not_active Expired
- 1968-06-20 CH CH930268A patent/CH512431A/it not_active IP Right Cessation
- 1968-06-27 FR FR1585414D patent/FR1585414A/fr not_active Expired
- 1968-07-24 BE BE718518D patent/BE718518A/xx unknown
- 1968-07-26 DE DE19681793040 patent/DE1793040A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES355063A2 (es) | 1969-11-16 |
| SE354852B (en)) | 1973-03-26 |
| IT1143626B (it) | 1986-10-22 |
| CH512431A (it) | 1971-09-15 |
| GB1188480A (en) | 1970-04-15 |
| DK127638B (da) | 1973-12-10 |
| BE718518A (en)) | 1969-01-24 |
| FR1585414A (en)) | 1970-01-23 |
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