BG61912B1 - Нов метод за получаване на 3,4-дихидрокси-5-нитробензалдехид - Google Patents

Нов метод за получаване на 3,4-дихидрокси-5-нитробензалдехид Download PDF

Info

Publication number: BG61912B1
Authority: BG; Bulgaria
Prior art keywords: nitrobenzaldehyde; dihydroxy; hydroxy; zinc chloride; hydrochloric acid
Prior art date: 1994-09-23

Application number

BG101309A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG101309A (en

Inventor

Reijo J. Baeckstroem

Original Assignee

Orion-Yhtymae Oy

Priority date (The priority date 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 date listed.)

1994-09-23

Filing date

1997-03-11

Publication date

1998-09-30

1997-03-11 Application filed by Orion-Yhtymae Oy filed Critical Orion-Yhtymae Oy

1997-10-31 Publication of BG101309A publication Critical patent/BG101309A/xx

1998-09-30 Publication of BG61912B1 publication Critical patent/BG61912B1/bg

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)

BG101309A 1994-09-23 1997-03-11 Нов метод за получаване на 3,4-дихидрокси-5-нитробензалдехид BG61912B1 (bg)

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)

* Cited by examiner, † Cited by third party
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
CN101631548B (zh) *	2007-01-31	2014-08-27	比艾尔-坡特拉有限公司	Comt抑制剂的单次药物剂量单元和药物组合物
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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NO107714C (cs) *	1961-06-21
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
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
CA2085137A1 (fr) *	1991-12-12	1993-06-13	Hoechst Marion Roussel	Nouvelles cephalosporines comportant en position 7 un radical benzyloxyimino substitue, leur procede de preparation, leur application comme medicaments
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 EP EP95930558A patent/EP0782559B1/en not_active Expired - Lifetime
- 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 DK DK95930558T patent/DK0782559T3/da active
- 1995-09-20 DE DE69507309T patent/DE69507309T2/de not_active Expired - Fee Related
- 1995-09-20 RO RO97-00574A patent/RO119540B1/ro unknown
- 1995-09-20 JP JP51063396A patent/JP3717933B2/ja not_active Expired - Fee Related
- 1995-09-20 CA CA002200227A patent/CA2200227C/en not_active Expired - Fee Related
- 1995-09-20 NZ NZ292187A patent/NZ292187A/en unknown
- 1995-09-20 SI SI9520102A patent/SI9520102A/sl not_active IP Right Cessation
- 1995-09-20 BR BR9508852A patent/BR9508852A/pt not_active IP Right Cessation
- 1995-09-20 US US08/809,405 patent/US5710343A/en not_active Expired - Fee Related
- 1995-09-20 SK SK378-97A patent/SK281789B6/sk unknown
- 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 WO PCT/FI1995/000513 patent/WO1996009274A1/en not_active Ceased
- 1995-09-20 AU AU33901/95A patent/AU684672B2/en not_active Ceased
- 1995-09-20 ES ES95930558T patent/ES2127552T3/es not_active Expired - Lifetime
- 1995-09-20 CN CN95195222A patent/CN1064673C/zh not_active Expired - Fee Related
- 1995-09-20 AT AT95930558T patent/ATE175660T1/de not_active IP Right Cessation
- 1995-09-20 PL PL95319348A patent/PL180016B1/pl not_active IP Right Cessation
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

Publication number	Publication date
IL115122A0 (en)	1995-12-08
CN1164852A (zh)	1997-11-12
LV11831A (lv)	1997-08-20
KR970706234A (ko)	1997-11-03
IL115122A (en)	1999-07-14
SI9520102A (en)	1997-08-31
BG101309A (en)	1997-10-31
PL319348A1 (en)	1997-08-04
CN1064673C (zh)	2001-04-18
EP0782559B1 (en)	1999-01-13
DE69507309D1 (de)	1999-02-25
JP3717933B2 (ja)	2005-11-16
NZ292187A (en)	1997-12-19
NO971325D0 (no)	1997-03-21
AU3390195A (en)	1996-04-09
DE69507309T2 (de)	1999-07-15
ATE175660T1 (de)	1999-01-15
SK37897A3 (en)	1997-11-05
JPH10505849A (ja)	1998-06-09
MX9702064A (es)	1997-10-31
GR3029815T3 (en)	1999-06-30
PL180016B1 (en)	2000-11-30
AU684672B2 (en)	1997-12-18
BR9508852A (pt)	1999-05-04
CZ288684B6 (cs)	2001-08-15
HU224821B1 (en)	2006-02-28
US5710343A (en)	1998-01-20
DK0782559T3 (da)	1999-08-30
LV11831B (en)	1997-12-20
CZ80097A3 (cs)	1998-03-18
CA2200227A1 (en)	1996-03-28
RO119540B1 (ro)	2004-12-30
RU2130449C1 (ru)	1999-05-20
NO306670B1 (no)	1999-12-06
NO971325L (no)	1997-03-21
CA2200227C (en)	2005-09-13
GB9419274D0 (en)	1994-11-09
HUT77441A (hu)	1998-04-28
EP0782559A1 (en)	1997-07-09
ES2127552T3 (es)	1999-04-16
SK281789B6 (sk)	2001-08-06
KR100368163B1 (ko)	2003-03-26
WO1996009274A1 (en)	1996-03-28

Publication	Publication Date	Title
KR850000945B1 (ko)	1985-06-29	5-카바모일-10-옥소-10, 11-디하이드로-5H-디벤즈[b, f]-아제핀의 제조방법
Ratajczak et al.	1975	Resolution of S-(1-ferrocenylethyl) thioglycolic acid. A new method of preparation of optically active 1-ferrocenylethanol
JPH0120145B2 (cs)	1989-04-14
RU2130449C1 (ru)	1999-05-20	Способ получения 3,4-дигидрокси-5-нитробензальдегида
US3574740A (en)	1971-04-13	Method of preparing methane sulfonamide and its derivatives
EP0456799B1 (en)	1994-06-01	Improved method of preparing an intermediate for the manufacture of bambuterol
FI114394B (fi)	2004-10-15	Uusi menetelmä 3,4-dihydroksi-5-nitrobentsaldehydin valmistamiseksi
Okawa et al.	1979	A convenient method of the synthesis of phosphopeptide via aziridine ring opening reaction.
EP0010262B1 (en)	1983-01-26	Process for preparing 3-amino-5-t-butylisoxazole
JPS62198665A (ja)	1987-09-02	キナルジンの精製法
JP4406294B2 (ja)	2010-01-27	Ｎ−（２−ブロモエチル）カルバミン酸ｔｅｒｔ−ブチルの製造方法
KR101170192B1 (ko)	2012-07-31	1,2-벤즈이속사졸-3-메탄술폰아미드의 원-포트 제조방법
EP0038641B1 (en)	1984-04-04	Process for producing d-2-amino-2-(1,4-cyclohexadienyl) acetic acid
RU2225391C2 (ru)	2004-03-10	Способ получения динитрила малоновой кислоты
JPS61227549A (ja)	1986-10-09	（±）−２−クロロブタン酸の光学分割法
SU108808A2 (ru)	1956-11-30	Способ получени d11-трео-1-паранитрофенил-2-амино-1,3-пропандиола
CF	0	Amalgamated Aluminium as a Neutral Reduciug Agent. By HANS WISLTCER'L'S and LUDWIG KAL'FbIaNN (Be?.., 18!) 5, 28, l..% 3--
JPH023628A (ja)	1990-01-09	光学活性１−メチル−３−フェニルプロピルアミンの製法
CH362087A (fr)	1962-05-31	Procédé de préparation d'un dipeptide
EP1431270A1 (en)	2004-06-23	A process for preparing 2-Nitro-4'-Fluorobenzophenone
JPH082867B2 (ja)	1996-01-17	フェニルクロロチオホルメイト類の製造法
BE851223A (fr)	1977-05-31	Procede de preparation de 5(6)-phenylsulfinyl-2-benzimidazol-carbamate de methyle
WO2006126255A1 (ja)	2006-11-30	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)	1980-01-31	Způsob výroby 2-methylthio-5-hydroxypyrimidinu
CH369761A (fr)	1963-06-15	Procédé de préparation d'une nouvelle tryptamine substituée