SK41297A3 - Method for preparing nitrobenzene derivatives - Google Patents

Method for preparing nitrobenzene derivatives Download PDF

Info

Publication number: SK41297A3
Authority: SK; Slovakia
Prior art keywords: formula; process according; carbon; compound; mol
Prior art date: 1994-09-29

Application number

SK412-97A

Other languages

English (en)

Slovak (sk)

Inventor

Franco Manfre

Original Assignee

Rhone Poulenc Rorer Sa

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.)

1994-09-29

Filing date

1995-09-27

Publication date

1997-11-05

1995-09-27 Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa

1997-11-05 Publication of SK41297A3 publication Critical patent/SK41297A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 22
150000005181 nitrobenzenes Chemical class 0.000 title claims description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 12
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
PTMFUWGXPRYYMC-UHFFFAOYSA-N triethylazanium;formate Chemical compound OC=O.CCN(CC)CC PTMFUWGXPRYYMC-UHFFFAOYSA-N 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 6
239000000460 chlorine Substances 0.000 claims abstract description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
238000009835 boiling Methods 0.000 claims abstract description 3
229910052799 carbon Inorganic materials 0.000 claims abstract description 3
229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
235000019253 formic acid Nutrition 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
239000012298 atmosphere Substances 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
229910052763 palladium Inorganic materials 0.000 abstract 1
239000012429 reaction media Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
ZUMGMEDTUNEISY-UHFFFAOYSA-N 2-(4-chloro-3-nitrophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(Cl)C([N+]([O-])=O)=C1 ZUMGMEDTUNEISY-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ACKABRICAWAUFX-UHFFFAOYSA-N 2-(4-chloro-3-nitrophenyl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=C(Cl)C([N+]([O-])=O)=C1 ACKABRICAWAUFX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
-1 alkali metal cyanide Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
UMVOCNFWVVRKKE-UHFFFAOYSA-N 2-(3-aminophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC(N)=C1 UMVOCNFWVVRKKE-UHFFFAOYSA-N 0.000 description 1
MSCZZRXBIBUPKG-UHFFFAOYSA-N 2-(3-nitrophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC([N+]([O-])=O)=C1 MSCZZRXBIBUPKG-UHFFFAOYSA-N 0.000 description 1
SSFDAZXGUKDEAH-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=C(Cl)C=C1 SSFDAZXGUKDEAH-UHFFFAOYSA-N 0.000 description 1
NICZEYWEIXUUKS-UHFFFAOYSA-N 2-methyl-2-(3-nitrophenyl)propanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=CC([N+]([O-])=O)=C1 NICZEYWEIXUUKS-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000000729 antidote Substances 0.000 description 1
229940075522 antidotes Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000005695 dehalogenation reaction Methods 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Classifications

- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK412-97A 1994-09-29 1995-09-27 Method for preparing nitrobenzene derivatives SK41297A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9411657A FR2725201B1 (fr)	1994-09-29	1994-09-29	Procede de preparation de derives du nitrobenzene
PCT/FR1995/001241 WO1996010010A1 (fr)	1994-09-29	1995-09-27	Procede de preparation de derives du nitrobenzene

Publications (1)

Publication Number	Publication Date
SK41297A3 true SK41297A3 (en)	1997-11-05

Family

ID=9467418

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK412-97A SK41297A3 (en)	1994-09-29	1995-09-27	Method for preparing nitrobenzene derivatives

Country Status (17)

Country	Link
US (1)	US5719317A (de)
EP (1)	EP0793639B1 (de)
JP (1)	JPH10506403A (de)
KR (1)	KR970706235A (de)
AT (1)	ATE175187T1 (de)
AU (1)	AU3570095A (de)
CA (1)	CA2197903A1 (de)
CZ (1)	CZ95597A3 (de)
DE (1)	DE69507049T2 (de)
DK (1)	DK0793639T3 (de)
ES (1)	ES2127559T3 (de)
FR (1)	FR2725201B1 (de)
MX (1)	MX9701802A (de)
PL (1)	PL319687A1 (de)
SK (1)	SK41297A3 (de)
WO (1)	WO1996010010A1 (de)
ZA (1)	ZA958142B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2212598C1 (ru) *	2002-02-26	2003-09-20	Горбачев Станислав Прокофьевич	Способ частичного сжижения природного газа и установка для его реализации
JP2015013832A (ja) *	2013-07-05	2015-01-22	日立化成株式会社	芳香族化合物の製造方法及び有機エレクトロニクス材料

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH480072A (de) *	1967-05-29	1969-10-31	Bracco Ind Chimica Spa	Neue Röntgenkontrastmittel und Verfahren zu ihrer Herstellung
US4659862A (en) *	1984-05-03	1987-04-21	E. I. Du Pont De Nemours And Company	Process of preparing nitrodihydroaryl carbonyl compounds
US4859232A (en) *	1986-12-05	1989-08-22	Monsanto Company	Substituted-aryl cyclopropanecarbonitriles and derivatives thereof as herbicide antidotes

1994
- 1994-09-29 FR FR9411657A patent/FR2725201B1/fr not_active Expired - Fee Related
1995
- 1995-09-27 WO PCT/FR1995/001241 patent/WO1996010010A1/fr not_active Ceased
- 1995-09-27 SK SK412-97A patent/SK41297A3/sk unknown
- 1995-09-27 US US08/809,778 patent/US5719317A/en not_active Expired - Fee Related
- 1995-09-27 ZA ZA958142A patent/ZA958142B/xx unknown
- 1995-09-27 KR KR1019970701984A patent/KR970706235A/ko not_active Withdrawn
- 1995-09-27 PL PL95319687A patent/PL319687A1/xx unknown
- 1995-09-27 EP EP95932796A patent/EP0793639B1/de not_active Expired - Lifetime
- 1995-09-27 AU AU35700/95A patent/AU3570095A/en not_active Abandoned
- 1995-09-27 JP JP8511447A patent/JPH10506403A/ja active Pending
- 1995-09-27 MX MX9701802A patent/MX9701802A/es unknown
- 1995-09-27 CA CA002197903A patent/CA2197903A1/fr not_active Abandoned
- 1995-09-27 DK DK95932796T patent/DK0793639T3/da active
- 1995-09-27 ES ES95932796T patent/ES2127559T3/es not_active Expired - Lifetime
- 1995-09-27 CZ CZ97955A patent/CZ95597A3/cs unknown
- 1995-09-27 DE DE69507049T patent/DE69507049T2/de not_active Expired - Fee Related
- 1995-09-27 AT AT95932796T patent/ATE175187T1/de active

Also Published As

Publication number	Publication date
US5719317A (en)	1998-02-17
ATE175187T1 (de)	1999-01-15
KR970706235A (ko)	1997-11-03
AU3570095A (en)	1996-04-19
MX9701802A (es)	1997-06-28
WO1996010010A1 (fr)	1996-04-04
FR2725201B1 (fr)	1996-11-15
DE69507049T2 (de)	1999-06-24
CZ95597A3 (en)	1997-07-16
ZA958142B (en)	1996-04-25
JPH10506403A (ja)	1998-06-23
CA2197903A1 (fr)	1996-04-04
ES2127559T3 (es)	1999-04-16
PL319687A1 (en)	1997-08-18
DE69507049D1 (de)	1999-02-11
EP0793639B1 (de)	1998-12-30
EP0793639A1 (de)	1997-09-10
DK0793639T3 (da)	1999-08-30
FR2725201A1 (fr)	1996-04-05

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