JPS6228133B2 - - Google Patents
Info
- Publication number
- JPS6228133B2 JPS6228133B2 JP14471679A JP14471679A JPS6228133B2 JP S6228133 B2 JPS6228133 B2 JP S6228133B2 JP 14471679 A JP14471679 A JP 14471679A JP 14471679 A JP14471679 A JP 14471679A JP S6228133 B2 JPS6228133 B2 JP S6228133B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- copper
- hydrogen atom
- reaction
- lower alkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001879 copper Chemical class 0.000 claims description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- IUJAAIZKRJJZGQ-UHFFFAOYSA-N 2-(2-chlorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1Cl IUJAAIZKRJJZGQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- -1 cuprous chloride anhydride Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000006606 n-butoxy group Chemical group 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- WINOEVFNWAEXIF-UHFFFAOYSA-N 4-methoxy-1,3-dihydroindol-2-one Chemical compound COC1=CC=CC2=C1CC(=O)N2 WINOEVFNWAEXIF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- QYCVHILLJSYYBD-UHFFFAOYSA-L copper;oxalate Chemical compound [Cu+2].[O-]C(=O)C([O-])=O QYCVHILLJSYYBD-UHFFFAOYSA-L 0.000 description 1
- FMWMEQINULDRBI-UHFFFAOYSA-L copper;sulfite Chemical compound [Cu+2].[O-]S([O-])=O FMWMEQINULDRBI-UHFFFAOYSA-L 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- KHBWTRFWQROKJZ-UHFFFAOYSA-N methyl 2-(2-chlorophenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1Cl KHBWTRFWQROKJZ-UHFFFAOYSA-N 0.000 description 1
- UBXWFYGCGHBNAP-UHFFFAOYSA-N methyl 2-bromo-2-(2-methoxyphenyl)acetate Chemical compound COC(=O)C(Br)C1=CC=CC=C1OC UBXWFYGCGHBNAP-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14471679A JPS5668668A (en) | 1979-11-08 | 1979-11-08 | Preparation of 2-indolinones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14471679A JPS5668668A (en) | 1979-11-08 | 1979-11-08 | Preparation of 2-indolinones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5668668A JPS5668668A (en) | 1981-06-09 |
| JPS6228133B2 true JPS6228133B2 (enrdf_load_stackoverflow) | 1987-06-18 |
Family
ID=15368630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14471679A Granted JPS5668668A (en) | 1979-11-08 | 1979-11-08 | Preparation of 2-indolinones |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5668668A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012020424A1 (en) | 2010-08-12 | 2012-02-16 | Arch Pharmalabs Limited | A short process for the preparation of ziprasidone and intermediates thereof |
-
1979
- 1979-11-08 JP JP14471679A patent/JPS5668668A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012020424A1 (en) | 2010-08-12 | 2012-02-16 | Arch Pharmalabs Limited | A short process for the preparation of ziprasidone and intermediates thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5668668A (en) | 1981-06-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0148911B2 (enrdf_load_stackoverflow) | ||
| JPS6228133B2 (enrdf_load_stackoverflow) | ||
| JPS5814428B2 (ja) | 立体異性脂環ジアミンの異性化法 | |
| JPS597699B2 (ja) | インドリン類の製造方法 | |
| JPS5949221B2 (ja) | ３−アシルアミノ−４−ホモイソツイスタンの製造法 | |
| US4521616A (en) | Method for the preparation of fluoroanthranilic acids | |
| JP2788221B2 (ja) | キノリン−２，３−ジカルボン酸の新規な製造方法 | |
| JP3771334B2 (ja) | ２−メチル−３−（３，４−メチレンジオキシフェニル）アクリルアルデヒドの製法 | |
| JPS632262B2 (enrdf_load_stackoverflow) | ||
| JPH07291934A (ja) | ５，７−ジクロロ−４−ヒドロキシキノリンの製造方法 | |
| EP0600714A1 (en) | Process for producing O,O'-diacyltartaric anhydride and process for producing O,O'-diacyltartaric acid | |
| JPS63211264A (ja) | インドリン類の製造法 | |
| JP2767295B2 (ja) | インドール―３―カルボニトリル化合物の製造方法 | |
| JP3563424B2 (ja) | ４ｈ−ピラン−４−オンの製造方法 | |
| JPH07206816A (ja) | ２，４，５−トリブロモピロール−３−カルボニトリルの調製方法 | |
| JP2689589B2 (ja) | 新規なアルコール類およびその製造法 | |
| EP0163506B1 (en) | Process for the preparation of a pyridil-propanoic acid | |
| EP0163948B1 (en) | Process for producing an indoline | |
| JPS5993059A (ja) | シトシン類の製法 | |
| JPS58172389A (ja) | １，２，５，６−テトラヒドロ−４−Ｈ−ピロロ〔３，２，１−ｉｊ〕−キノリン−４−オンの製造方法 | |
| JPS6316374B2 (enrdf_load_stackoverflow) | ||
| JPH0324045A (ja) | クロロマレエートまたはクロロフマレートまたはそれらの混合物を経るアニリノフマレートの製造方法 | |
| JPS638104B2 (enrdf_load_stackoverflow) | ||
| JPS6343382B2 (enrdf_load_stackoverflow) | ||
| JPH0461862B2 (enrdf_load_stackoverflow) |