CH636336A5 - Process for the synthesis of malonic acid derivatives - Google Patents

Process for the synthesis of malonic acid derivatives Download PDF

Info

Publication number: CH636336A5
Authority: CH; Switzerland
Prior art keywords: process according; alkyl; aryl; formula; palladium
Prior art date: 1977-02-24

Application number

CH141378A

Other languages

English (en)

Italian (it)

Inventor

Ugo Romano

Franco Rivelli

Original Assignee

Anic Spa

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.)

1977-02-24

Filing date

1978-02-08

Publication date

1983-05-31

1978-02-08 Application filed by Anic Spa filed Critical Anic Spa

1983-05-31 Publication of CH636336A5 publication Critical patent/CH636336A5/it

Links

238000000034 method Methods 0.000 title claims description 20
230000015572 biosynthetic process Effects 0.000 title claims description 4
238000003786 synthesis reaction Methods 0.000 title claims description 4
150000002690 malonic acid derivatives Chemical class 0.000 title claims description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
-1 aliphatic tertiary amines Chemical class 0.000 claims description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 5
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
150000001342 alkaline earth metals Chemical class 0.000 claims description 4
125000002877 alkyl aryl group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
150000007942 carboxylates Chemical class 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000002560 nitrile group Chemical group 0.000 claims description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
150000007529 inorganic bases Chemical group 0.000 claims description 3
150000007530 organic bases Chemical group 0.000 claims description 3
150000002940 palladium Chemical class 0.000 claims description 3
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
150000001346 alkyl aryl ethers Chemical class 0.000 claims description 2
125000000129 anionic group Chemical group 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
150000001983 dialkylethers Chemical class 0.000 claims description 2
150000002334 glycols Chemical class 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
150000002825 nitriles Chemical class 0.000 claims description 2
150000003003 phosphines Chemical class 0.000 claims description 2
150000003222 pyridines Chemical class 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
230000003213 activating effect Effects 0.000 claims 2
239000000010 aprotic solvent Substances 0.000 claims 2
239000002798 polar solvent Substances 0.000 claims 2
239000000126 substance Substances 0.000 claims 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
239000002585 base Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
MVSDGUKSWHYVHB-UHFFFAOYSA-N phosphane;cyanide Chemical class P.N#[C-] MVSDGUKSWHYVHB-UHFFFAOYSA-N 0.000 claims 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
WVYQRIZVVUSKAV-UHFFFAOYSA-N C(C)N(C(CC(=O)NCC)=O)CC Chemical compound C(C)N(C(CC(=O)NCC)=O)CC WVYQRIZVVUSKAV-UHFFFAOYSA-N 0.000 description 1
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
229940125717 barbiturate Drugs 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000003326 hypnotic agent Substances 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
150000002527 isonitriles Chemical class 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
150000002941 palladium compounds Chemical class 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
CZMAXQOXGAWNDO-UHFFFAOYSA-N propane-1,1,2-triol Chemical compound CC(O)C(O)O CZMAXQOXGAWNDO-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH141378A 1977-02-24 1978-02-08 Process for the synthesis of malonic acid derivatives CH636336A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT2064177A IT1075123B (it)	1977-02-24	1977-02-24	Processo per la preparazione di derivati dell'acido malonico

Publications (1)

Publication Number	Publication Date
CH636336A5 true CH636336A5 (en)	1983-05-31

Family

ID=11169929

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH141378A CH636336A5 (en)	1977-02-24	1978-02-08	Process for the synthesis of malonic acid derivatives

Country Status (7)

Country	Link
CH (1)	CH636336A5 (cs)
CS (1)	CS207500B1 (cs)
DD (1)	DD134083A5 (cs)
DE (1)	DE2807625C2 (cs)
FR (1)	FR2381738A1 (cs)
GB (1)	GB1574113A (cs)
IT (1)	IT1075123B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2907873A1 (de) *	1979-03-01	1980-09-11	Dynamit Nobel Ag	Verfahren zur herstellung von n-propylcyanessigsaeureestern
CN110950757B (zh) *	2019-12-26	2021-11-23	中国科学院兰州化学物理研究所	一种丙二酸二酯的生产方法及系统
CN117658812A (zh) *	2022-08-26	2024-03-08	鞍山七彩化学股份有限公司	一种丙二酸酯的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2359963C2 (de) *	1973-12-01	1982-01-28	Dynamit Nobel Ag, 5210 Troisdorf	Verfahren zur Herstellung von Malonsäuredialkylestern
DE2403483A1 (de) *	1974-01-25	1975-08-07	Dynamit Nobel Ag	Verfahren zur herstellung von cyanessigsaeurealkylestern
DE2509017C2 (de) *	1975-03-01	1983-03-03	Dynamit Nobel Ag, 5210 Troisdorf	Verfahren zur Herstellung von Phenylmalonsäuredialkylestern

1977
- 1977-02-24 IT IT2064177A patent/IT1075123B/it active
1978
- 1978-02-06 GB GB473978A patent/GB1574113A/en not_active Expired
- 1978-02-08 CH CH141378A patent/CH636336A5/it not_active IP Right Cessation
- 1978-02-15 CS CS96678A patent/CS207500B1/cs unknown
- 1978-02-22 DD DD20379778A patent/DD134083A5/xx unknown
- 1978-02-22 DE DE19782807625 patent/DE2807625C2/de not_active Expired
- 1978-02-23 FR FR7805250A patent/FR2381738A1/fr active Granted

Also Published As

Publication number	Publication date
FR2381738B1 (cs)	1981-07-31
DD134083A5 (de)	1979-02-07
DE2807625A1 (de)	1978-08-31
IT1075123B (it)	1985-04-22
GB1574113A (en)	1980-09-03
CS207500B1 (en)	1981-07-31
FR2381738A1 (fr)	1978-09-22
DE2807625C2 (de)	1982-07-01

Legal Events

Date	Code	Title	Description
1984-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

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