CH441269A - Verfahren zur Herstellung von substituierten 3,4-Dihydroxy-benzoesäureestern - Google Patents
Verfahren zur Herstellung von substituierten 3,4-Dihydroxy-benzoesäureesternInfo
- Publication number
- CH441269A CH441269A CH1357262A CH1357262A CH441269A CH 441269 A CH441269 A CH 441269A CH 1357262 A CH1357262 A CH 1357262A CH 1357262 A CH1357262 A CH 1357262A CH 441269 A CH441269 A CH 441269A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- methyl
- substituted
- methoxy
- acid esters
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- -1 N-substituted glycolic acid amides Chemical class 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 206010002091 Anaesthesia Diseases 0.000 description 8
- 230000037005 anaesthesia Effects 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000003444 anaesthetic effect Effects 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- MWAYRGBWOVHDDZ-UHFFFAOYSA-N Ethyl vanillate Chemical compound CCOC(=O)C1=CC=C(O)C(OC)=C1 MWAYRGBWOVHDDZ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- SISPKDDUECPIEH-UHFFFAOYSA-N 2-chloro-N-ethoxy-N-ethylacetamide Chemical compound C(C)N(C(CCl)=O)OCC SISPKDDUECPIEH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- BVWTXUYLKBHMOX-UHFFFAOYSA-N methyl vanillate Chemical compound COC(=O)C1=CC=C(O)C(OC)=C1 BVWTXUYLKBHMOX-UHFFFAOYSA-N 0.000 description 2
- 239000004081 narcotic agent Substances 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- YMQRPXBBBOXHNZ-UHFFFAOYSA-N 2-chloro-1-morpholin-4-ylethanone Chemical compound ClCC(=O)N1CCOCC1 YMQRPXBBBOXHNZ-UHFFFAOYSA-N 0.000 description 1
- CQQUWTMMFMJEFE-UHFFFAOYSA-N 2-chloro-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CCl CQQUWTMMFMJEFE-UHFFFAOYSA-N 0.000 description 1
- IRJPOHGFTJECRO-UHFFFAOYSA-N 5-cyclohexyl-1,5-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1CCCCC1 IRJPOHGFTJECRO-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- PFYHAAAQPNMZHO-UHFFFAOYSA-N Methyl 2-methoxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OC PFYHAAAQPNMZHO-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0035614 | 1961-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH441269A true CH441269A (de) | 1967-08-15 |
Family
ID=7096071
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1357262A CH441269A (de) | 1961-12-21 | 1962-11-20 | Verfahren zur Herstellung von substituierten 3,4-Dihydroxy-benzoesäureestern |
| CH1797366A CH441271A (de) | 1961-12-21 | 1962-11-20 | Verfahren zur Herstellung von substituierten 3,4-Dihydroxybenzoesäureestern |
| CH1797466A CH441272A (de) | 1961-12-21 | 1962-11-20 | Verfahren zur Herstellung von substituierten 3,4-Dihydroxybenzoesäureestern |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1797366A CH441271A (de) | 1961-12-21 | 1962-11-20 | Verfahren zur Herstellung von substituierten 3,4-Dihydroxybenzoesäureestern |
| CH1797466A CH441272A (de) | 1961-12-21 | 1962-11-20 | Verfahren zur Herstellung von substituierten 3,4-Dihydroxybenzoesäureestern |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3274187A (index.php) |
| AT (1) | AT246122B (index.php) |
| CH (3) | CH441269A (index.php) |
| DK (3) | DK108855C (index.php) |
| FR (2) | FR1509911A (index.php) |
| GB (1) | GB959264A (index.php) |
| NL (1) | NL286942A (index.php) |
| SE (3) | SE310878B (index.php) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1915334A (en) * | 1930-10-16 | 1933-06-27 | Du Pont | Fluosilicate of organic heterocyclic bases and process of making it |
| US2075359A (en) * | 1930-10-16 | 1937-03-30 | Du Pont | Insecticide |
| US2425320A (en) * | 1942-10-23 | 1947-08-12 | Koppers Co Inc | Cleaning and pickling of metals |
| US2606155A (en) * | 1946-11-26 | 1952-08-05 | Koppers Co Inc | Cleaning and pickling composition for metals |
| US2868689A (en) * | 1956-10-09 | 1959-01-13 | Allied Lab Inc | Pharmaceutical preparations containing dyclonine hydrochloride and chlorobutanol |
| US2867619A (en) * | 1956-11-05 | 1959-01-06 | Lakeside Lab Inc | Aminoalkynyl-n-alkylpiperidine carboxylates |
| US2969386A (en) * | 1957-04-29 | 1961-01-24 | Mobay Chemical Corp | Production of polyurethanepolyisocyanates |
| US3034958A (en) * | 1960-01-26 | 1962-05-15 | Ortho Pharma Corp | Soporific compositions |
-
1962
- 1962-11-20 CH CH1357262A patent/CH441269A/de unknown
- 1962-11-20 CH CH1797366A patent/CH441271A/de unknown
- 1962-11-20 CH CH1797466A patent/CH441272A/de unknown
- 1962-12-06 GB GB46097/62A patent/GB959264A/en not_active Expired
- 1962-12-07 AT AT100464A patent/AT246122B/de active
- 1962-12-19 DK DK95264AA patent/DK108855C/da active
- 1962-12-19 DK DK95164AA patent/DK107023C/da active
- 1962-12-19 US US245658A patent/US3274187A/en not_active Expired - Lifetime
- 1962-12-19 NL NL286942D patent/NL286942A/xx unknown
- 1962-12-19 DK DK553762AA patent/DK107223C/da active
- 1962-12-20 SE SE463/65A patent/SE310878B/xx unknown
- 1962-12-20 SE SE13805/62A patent/SE311149B/xx unknown
- 1962-12-21 FR FR919511A patent/FR1509911A/fr not_active Expired
-
1963
- 1963-03-20 FR FR928644A patent/FR2927M/fr not_active Expired
-
1965
- 1965-01-14 SE SE464/65A patent/SE310664B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK108855C (da) | 1968-02-19 |
| DK107023C (da) | 1967-04-17 |
| FR2927M (index.php) | 1964-12-18 |
| GB959264A (en) | 1964-05-27 |
| US3274187A (en) | 1966-09-20 |
| SE310878B (index.php) | 1969-05-19 |
| NL286942A (index.php) | 1965-02-25 |
| AT246122B (de) | 1966-04-12 |
| CH441272A (de) | 1967-08-15 |
| DK107223C (da) | 1967-05-08 |
| FR1509911A (fr) | 1968-01-19 |
| SE310664B (index.php) | 1969-05-12 |
| CH441271A (de) | 1967-08-15 |
| SE311149B (index.php) | 1969-06-02 |
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