BG61912B1 - Нов метод за получаване на 3,4-дихидрокси-5-нитробензалдехид - Google Patents
Нов метод за получаване на 3,4-дихидрокси-5-нитробензалдехид Download PDFInfo
- Publication number
- BG61912B1 BG61912B1 BG101309A BG10130997A BG61912B1 BG 61912 B1 BG61912 B1 BG 61912B1 BG 101309 A BG101309 A BG 101309A BG 10130997 A BG10130997 A BG 10130997A BG 61912 B1 BG61912 B1 BG 61912B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- nitrobenzaldehyde
- dihydroxy
- hydroxy
- zinc chloride
- hydrochloric acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910001868 water Inorganic materials 0.000 claims abstract description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 235000005074 zinc chloride Nutrition 0.000 claims description 12
- 239000011592 zinc chloride Substances 0.000 claims description 12
- MDWLNBVKBMKTKN-UHFFFAOYSA-N 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde Chemical compound CCOC1=CC(C=O)=CC([N+]([O-])=O)=C1O MDWLNBVKBMKTKN-UHFFFAOYSA-N 0.000 claims description 9
- BBFJODMCHICIAA-UHFFFAOYSA-N 3,4-dihydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC(C=O)=CC([N+]([O-])=O)=C1O BBFJODMCHICIAA-UHFFFAOYSA-N 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 3
- IPCXNCATNBAPKW-UHFFFAOYSA-N zinc;hydrate Chemical compound O.[Zn] IPCXNCATNBAPKW-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- ZEHYRTJBFMZHCY-UHFFFAOYSA-N 5-nitrovanillin Chemical compound COC1=CC(C=O)=CC([N+]([O-])=O)=C1O ZEHYRTJBFMZHCY-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006900 dealkylation reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000020335 dealkylation Effects 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 238000010520 demethylation reaction Methods 0.000 description 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RCCIQDAGHPKBOM-UHFFFAOYSA-N 2-bromo-3,4-dihydroxy-5-nitrobenzaldehyde Chemical compound OC1=C(O)C([N+]([O-])=O)=CC(C=O)=C1Br RCCIQDAGHPKBOM-UHFFFAOYSA-N 0.000 description 1
- -1 5-substituted-3-nitrocatechol structure Chemical group 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- JRURYQJSLYLRLN-BJMVGYQFSA-N entacapone Chemical compound CCN(CC)C(=O)C(\C#N)=C\C1=CC(O)=C(O)C([N+]([O-])=O)=C1 JRURYQJSLYLRLN-BJMVGYQFSA-N 0.000 description 1
- 229960003337 entacapone Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9419274A GB9419274D0 (en) | 1994-09-23 | 1994-09-23 | New method for the preparation of 3,4-dihydroxy-5-nitrobenzaldehyde |
| PCT/FI1995/000513 WO1996009274A1 (en) | 1994-09-23 | 1995-09-20 | New method for the preparation of 3,4-dihydroxy-5-nitrobenzaldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG101309A BG101309A (en) | 1997-10-31 |
| BG61912B1 true BG61912B1 (bg) | 1998-09-30 |
Family
ID=10761838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG101309A BG61912B1 (bg) | 1994-09-23 | 1997-03-11 | Нов метод за получаване на 3,4-дихидрокси-5-нитробензалдехид |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5710343A (cs) |
| EP (1) | EP0782559B1 (cs) |
| JP (1) | JP3717933B2 (cs) |
| KR (1) | KR100368163B1 (cs) |
| CN (1) | CN1064673C (cs) |
| AT (1) | ATE175660T1 (cs) |
| AU (1) | AU684672B2 (cs) |
| BG (1) | BG61912B1 (cs) |
| BR (1) | BR9508852A (cs) |
| CA (1) | CA2200227C (cs) |
| CZ (1) | CZ288684B6 (cs) |
| DE (1) | DE69507309T2 (cs) |
| DK (1) | DK0782559T3 (cs) |
| ES (1) | ES2127552T3 (cs) |
| GB (1) | GB9419274D0 (cs) |
| GR (1) | GR3029815T3 (cs) |
| HU (1) | HU224821B1 (cs) |
| IL (1) | IL115122A (cs) |
| LV (1) | LV11831B (cs) |
| MX (1) | MX9702064A (cs) |
| NO (1) | NO306670B1 (cs) |
| NZ (1) | NZ292187A (cs) |
| PL (1) | PL180016B1 (cs) |
| RO (1) | RO119540B1 (cs) |
| RU (1) | RU2130449C1 (cs) |
| SI (1) | SI9520102A (cs) |
| SK (1) | SK281789B6 (cs) |
| WO (1) | WO1996009274A1 (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9419274D0 (en) * | 1994-09-23 | 1994-11-09 | Orion Yhtymae Oy | New method for the preparation of 3,4-dihydroxy-5-nitrobenzaldehyde |
| PT2124947T (pt) * | 2007-01-31 | 2017-10-25 | BIAL-PORTELA & Cª S A | Regime posológico para inibidores da comt |
| EP2251323B1 (en) | 2009-05-14 | 2014-04-23 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Method for the purification of entacapone |
| CN102633646B (zh) * | 2012-04-10 | 2014-06-04 | 中国海洋大学 | 一种新的5-硝基水杨醛制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1330382A (fr) * | 1961-06-21 | 1963-06-21 | Monsanto Chemicals | Procédé de clivage des éthers d'alcoyle o-hydroxyphényle et de préparation simultanée de composés 1-alkyl-2,3-dihydroxyphényliques |
| NL129847C (cs) * | 1961-06-21 | |||
| US4213920A (en) * | 1977-07-06 | 1980-07-22 | Ciba-Geigy Corporation | Process for the production of substituted benzaldehydes |
| DK175069B1 (da) * | 1986-03-11 | 2004-05-24 | Hoffmann La Roche | Pyrocatecholderivater |
| YU213587A (en) * | 1986-11-28 | 1989-06-30 | Orion Yhtymae Oy | Process for obtaining new pharmacologic active cateholic derivatives |
| DE4012008A1 (de) * | 1990-04-13 | 1991-10-17 | Bayer Ag | Verfahren zur herstellung von o-hydroxy-benzaldehyden |
| GB9113431D0 (en) * | 1991-06-20 | 1991-08-07 | Orion Yhytma Oy | Method for the preparation of 3,4-dihydroxy-5-nitrobenzaldehyde |
| EP0551034B1 (fr) * | 1991-12-12 | 2000-09-20 | Hoechst Marion Roussel | Céphalosporines antibiotiques comportant en position 7 un radical benzyloxyimino substitué |
| GB9419274D0 (en) * | 1994-09-23 | 1994-11-09 | Orion Yhtymae Oy | New method for the preparation of 3,4-dihydroxy-5-nitrobenzaldehyde |
-
1994
- 1994-09-23 GB GB9419274A patent/GB9419274D0/en active Pending
-
1995
- 1995-05-22 KR KR1019970701878A patent/KR100368163B1/ko not_active Expired - Fee Related
- 1995-08-31 IL IL11512295A patent/IL115122A/xx not_active IP Right Cessation
- 1995-09-20 SK SK378-97A patent/SK281789B6/sk unknown
- 1995-09-20 CA CA002200227A patent/CA2200227C/en not_active Expired - Fee Related
- 1995-09-20 DK DK95930558T patent/DK0782559T3/da active
- 1995-09-20 BR BR9508852A patent/BR9508852A/pt not_active IP Right Cessation
- 1995-09-20 WO PCT/FI1995/000513 patent/WO1996009274A1/en not_active Ceased
- 1995-09-20 US US08/809,405 patent/US5710343A/en not_active Expired - Fee Related
- 1995-09-20 CN CN95195222A patent/CN1064673C/zh not_active Expired - Fee Related
- 1995-09-20 AU AU33901/95A patent/AU684672B2/en not_active Ceased
- 1995-09-20 SI SI9520102A patent/SI9520102A/sl not_active IP Right Cessation
- 1995-09-20 PL PL95319348A patent/PL180016B1/pl not_active IP Right Cessation
- 1995-09-20 CZ CZ1997800A patent/CZ288684B6/cs not_active IP Right Cessation
- 1995-09-20 RU RU97106330A patent/RU2130449C1/ru not_active IP Right Cessation
- 1995-09-20 MX MX9702064A patent/MX9702064A/es not_active IP Right Cessation
- 1995-09-20 HU HU9702258A patent/HU224821B1/hu unknown
- 1995-09-20 RO RO97-00574A patent/RO119540B1/ro unknown
- 1995-09-20 AT AT95930558T patent/ATE175660T1/de not_active IP Right Cessation
- 1995-09-20 JP JP51063396A patent/JP3717933B2/ja not_active Expired - Fee Related
- 1995-09-20 DE DE69507309T patent/DE69507309T2/de not_active Expired - Fee Related
- 1995-09-20 NZ NZ292187A patent/NZ292187A/en unknown
- 1995-09-20 ES ES95930558T patent/ES2127552T3/es not_active Expired - Lifetime
- 1995-09-20 EP EP95930558A patent/EP0782559B1/en not_active Expired - Lifetime
-
1997
- 1997-03-11 BG BG101309A patent/BG61912B1/bg unknown
- 1997-03-21 NO NO971325A patent/NO306670B1/no unknown
- 1997-04-03 LV LVP-97-54A patent/LV11831B/en unknown
-
1999
- 1999-03-30 GR GR990400905T patent/GR3029815T3/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR850000945B1 (ko) | 5-카바모일-10-옥소-10, 11-디하이드로-5H-디벤즈[b, f]-아제핀의 제조방법 | |
| Ratajczak et al. | Resolution of S-(1-ferrocenylethyl) thioglycolic acid. A new method of preparation of optically active 1-ferrocenylethanol | |
| CN116621792A (zh) | 一种制备n-正丁基-1,2-苯并异噻唑啉-3-酮-1-氧化物的方法 | |
| BG61912B1 (bg) | Нов метод за получаване на 3,4-дихидрокси-5-нитробензалдехид | |
| US3574740A (en) | Method of preparing methane sulfonamide and its derivatives | |
| EP0456799B1 (en) | Improved method of preparing an intermediate for the manufacture of bambuterol | |
| FI114394B (fi) | Uusi menetelmä 3,4-dihydroksi-5-nitrobentsaldehydin valmistamiseksi | |
| Okawa et al. | A convenient method of the synthesis of phosphopeptide via aziridine ring opening reaction. | |
| US4154757A (en) | Process for the manufacture of p-hydroxybenzyl cyanide | |
| JPS62198665A (ja) | キナルジンの精製法 | |
| JP4406294B2 (ja) | Ｎ−（２−ブロモエチル）カルバミン酸ｔｅｒｔ−ブチルの製造方法 | |
| EP0010262B1 (en) | Process for preparing 3-amino-5-t-butylisoxazole | |
| KR101170192B1 (ko) | 1,2-벤즈이속사졸-3-메탄술폰아미드의 원-포트 제조방법 | |
| EP0038641B1 (en) | Process for producing d-2-amino-2-(1,4-cyclohexadienyl) acetic acid | |
| RU2225391C2 (ru) | Способ получения динитрила малоновой кислоты | |
| JPS61227549A (ja) | （±）−２−クロロブタン酸の光学分割法 | |
| CH616424A5 (cs) | ||
| SU108808A2 (ru) | Способ получени d11-трео-1-паранитрофенил-2-амино-1,3-пропандиола | |
| CF | Amalgamated Aluminium as a Neutral Reduciug Agent. By HANS WISLTCER'L'S and LUDWIG KAL'FbIaNN (Be?.., 18!) 5, 28, l..% 3-- | |
| CH362087A (fr) | Procédé de préparation d'un dipeptide | |
| JPH07157475A (ja) | （＋）−３−フェニル−５−｛２−（１−ピロリジニルメチル）ブチリル｝イソオキサゾール及びその塩の分割法 | |
| JPH082867B2 (ja) | フェニル クロロチオホルメイト類の製造法 | |
| BE851223A (fr) | Procede de preparation de 5(6)-phenylsulfinyl-2-benzimidazol-carbamate de methyle | |
| WO2006126255A1 (ja) | Ｎ－（２－ブロモエチル）カルバミン酸ｔｅｒｔ－ブチルの製造方法 | |
| CS195210B1 (cs) | Způsob výroby 2-methylthio-5-hydroxypyrimidinu |