IL45543A - Process for the preparation of indolyl-lactic acid - Google Patents

Process for the preparation of indolyl-lactic acid

Info

Publication number: IL45543A
Authority: IL; Israel
Prior art keywords: acid; process according; indolyl; preparation; phenyl
Prior art date: 1973-09-13

Application number

IL45543A

Other languages

English (en)

Other versions

IL45543A0 (en

Original Assignee

Lonza Ag

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.)

1973-09-13

Filing date

1974-08-26

Publication date

1977-07-31

1974-08-26 Application filed by Lonza Ag filed Critical Lonza Ag

1974-11-29 Publication of IL45543A0 publication Critical patent/IL45543A0/xx

1977-07-31 Publication of IL45543A publication Critical patent/IL45543A/en

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 6
PDFPULXGOHJQKA-UHFFFAOYSA-N 2-hydroxy-2-(1h-indol-2-yl)propanoic acid Chemical compound C1=CC=C2NC(C(O)(C(O)=O)C)=CC2=C1 PDFPULXGOHJQKA-UHFFFAOYSA-N 0.000 title claims 3
239000002253 acid Substances 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
239000001117 sulphuric acid Substances 0.000 claims description 5
235000011149 sulphuric acid Nutrition 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 2
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 3
229940067157 phenylhydrazine Drugs 0.000 claims 3
CNFPMOBLESHVCT-UHFFFAOYSA-N 2,3-dihydrofuran-2,5-dicarboxylic acid Chemical compound OC(=O)C1CC=C(C(O)=O)O1 CNFPMOBLESHVCT-UHFFFAOYSA-N 0.000 claims 2
239000000243 solution Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000013078 crystal Substances 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
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 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000004310 lactic acid Substances 0.000 description 2
235000014655 lactic acid Nutrition 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 1
-1 alkali metal salt Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
ICYOLCFDSJJLAC-UHFFFAOYSA-N gramine Chemical compound C1=CC=C[C]2C(CN(C)C)=CN=C21 ICYOLCFDSJJLAC-UHFFFAOYSA-N 0.000 description 1
GOERTRUXQHDLHC-UHFFFAOYSA-N gramine Natural products COC1=CC=C2NC=C(CN(C)C)C2=C1 GOERTRUXQHDLHC-UHFFFAOYSA-N 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

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

IL45543A 1973-09-13 1974-08-26 Process for the preparation of indolyl-lactic acid IL45543A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1317173A CH577967A5 (it)	1973-09-13	1973-09-13

Publications (2)

Publication Number	Publication Date
IL45543A0 IL45543A0 (en)	1974-11-29
IL45543A true IL45543A (en)	1977-07-31

Family

ID=4389973

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL45543A IL45543A (en)	1973-09-13	1974-08-26	Process for the preparation of indolyl-lactic acid

Country Status (15)

Country	Link
US (1)	US4190585A (it)
JP (1)	JPS5076068A (it)
AT (1)	AT337172B (it)
BE (1)	BE819898A (it)
CA (1)	CA1041522A (it)
CH (1)	CH577967A5 (it)
DD (1)	DD113532A5 (it)
DE (1)	DE2440419A1 (it)
FR (1)	FR2243941B1 (it)
GB (1)	GB1418599A (it)
IL (1)	IL45543A (it)
IT (1)	IT1032076B (it)
LU (1)	LU70900A1 (it)
NL (1)	NL7411522A (it)
SU (1)	SU521840A3 (it)

1973
- 1973-09-13 CH CH1317173A patent/CH577967A5/xx not_active IP Right Cessation
1974
- 1974-08-19 GB GB3637274A patent/GB1418599A/en not_active Expired
- 1974-08-23 DE DE2440419A patent/DE2440419A1/de not_active Withdrawn
- 1974-08-26 IL IL45543A patent/IL45543A/en unknown
- 1974-08-29 NL NL7411522A patent/NL7411522A/xx not_active Application Discontinuation
- 1974-09-11 SU SU2058461A patent/SU521840A3/ru active
- 1974-09-11 JP JP49105452A patent/JPS5076068A/ja active Pending
- 1974-09-11 IT IT7452970Q patent/IT1032076B/it active
- 1974-09-12 AT AT737874A patent/AT337172B/de not_active IP Right Cessation
- 1974-09-13 DD DD181083A patent/DD113532A5/xx unknown
- 1974-09-13 LU LU70900A patent/LU70900A1/xx unknown
- 1974-09-13 CA CA209,170A patent/CA1041522A/en not_active Expired
- 1974-09-13 BE BE148507A patent/BE819898A/xx unknown
- 1974-09-13 US US05/505,566 patent/US4190585A/en not_active Expired - Lifetime
- 1974-09-13 FR FR7431084A patent/FR2243941B1/fr not_active Expired

Also Published As

Publication number	Publication date
BE819898A (fr)	1975-03-13
US4190585A (en)	1980-02-26
DD113532A5 (it)	1975-06-12
AT337172B (de)	1977-06-10
GB1418599A (en)	1975-12-24
FR2243941A1 (it)	1975-04-11
CH577967A5 (it)	1976-07-30
LU70900A1 (it)	1975-05-28
IT1032076B (it)	1979-05-30
CA1041522A (en)	1978-10-31
ATA737874A (de)	1976-10-15
FR2243941B1 (it)	1977-11-04
JPS5076068A (it)	1975-06-21
SU521840A3 (ru)	1976-07-15
DE2440419A1 (de)	1975-03-27
NL7411522A (nl)	1975-03-17
IL45543A0 (en)	1974-11-29

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JPS60237041A (ja)	1985-11-25	３−プロピオニルサリチル酸誘導体の製造法
US2688015A (en)	1954-08-31	Manufacture of sulfamerazine
US3347864A (en)	1967-10-17	Production of aminoquinolines
JPS6026395B2 (ja)	1985-06-24	Ｎ−トリアルキルシリルメチル尿素の合成法
JP2885537B2 (ja)	1999-04-26	トラン誘導体の製造法
SU523090A1 (ru)	1976-07-30	Способ получени производных хиназолина
JPH0859652A (ja)	1996-03-05	チオフェン−２、５−ジカルボン酸およびそのジクロリドの製造方法
SU118821A1 (ru)	1958-11-30	Способ получени гетероауксина из грамина
RU1797608C (ru)	1993-02-23	Способ получени 2а-метил-транс-декагидрохинолона-4