JPS55133357A - Preparation of 1-cyano-2-hydroxy-3-phthalimidopropane - Google Patents
Preparation of 1-cyano-2-hydroxy-3-phthalimidopropaneInfo
- Publication number
- JPS55133357A JPS55133357A JP3994279A JP3994279A JPS55133357A JP S55133357 A JPS55133357 A JP S55133357A JP 3994279 A JP3994279 A JP 3994279A JP 3994279 A JP3994279 A JP 3994279A JP S55133357 A JPS55133357 A JP S55133357A
- Authority
- JP
- Japan
- Prior art keywords
- phthalimide
- epichlorohydrin
- phthalimidopropane
- hydroxy
- reaction
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title abstract 2
- FFQXXXBBRKUSHT-UHFFFAOYSA-N 4-(1,3-dioxoisoindol-2-yl)-3-hydroxybutanenitrile Chemical compound C1=CC=C2C(=O)N(CC(CC#N)O)C(=O)C2=C1 FFQXXXBBRKUSHT-UHFFFAOYSA-N 0.000 title 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N Phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000011780 sodium chloride Substances 0.000 abstract 3
- KBRVYEPWGIQEOF-UHFFFAOYSA-N 2-(3-chloro-2-hydroxypropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CC(CCl)O)C(=O)C2=C1 KBRVYEPWGIQEOF-UHFFFAOYSA-N 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- -1 Na salt Chemical compound 0.000 abstract 1
- 229960002298 aminohydroxybutyric acid Drugs 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- JMHRGKDWGWORNU-UHFFFAOYSA-M sodium;2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate Chemical compound [Na+].CC1=C(CC([O-])=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 JMHRGKDWGWORNU-UHFFFAOYSA-M 0.000 abstract 1
- YQGDEPYYFWUPGO-UHFFFAOYSA-N γ-amino-β-hydroxybutyric acid zwitterion Chemical compound [NH3+]CC(O)CC([O-])=O YQGDEPYYFWUPGO-UHFFFAOYSA-N 0.000 abstract 1
Abstract
PURPOSE: To obtain the high purity title compound in high yield without the specific preparation of a catalyst, the reaction of epichlorohydrin and phthalimide in the presence of an excess amount of epichlorohydrin using a metal salt of phthalimide as a catalyst.
CONSTITUTION: The reaction of epichlorohydrin and phthalimide gives 1-chloro-2- hydroxy-3-phthalimidopropane, to which a cyanide is added to afford the title compound. The reaction is carried out in the presence of an excess amount of epichlorohydrin, using a metal salt of phthalimide (e.g. Na salt, K salt, etc. of phthalimide) as a catalyst. The yield of 1-chloro-2-hydroxy-3-phthalimidopropane is 88W95%. The yield of the title compound is 86W92% and the purity is 98%. The reaction process can be simplified and the isolation is facilitated.
USE: Intermediate of γ-amino-β-hydroxybutyric acid.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3994279A JPS6317060B2 (en) | 1979-04-02 | 1979-04-02 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3994279A JPS6317060B2 (en) | 1979-04-02 | 1979-04-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55133357A true JPS55133357A (en) | 1980-10-17 |
| JPS6317060B2 JPS6317060B2 (en) | 1988-04-12 |
Family
ID=12566999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3994279A Expired JPS6317060B2 (en) | 1979-04-02 | 1979-04-02 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6317060B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999024393A1 (en) * | 1997-11-07 | 1999-05-20 | Pharmacia & Upjohn Company | Process to produce oxazolidinones |
| JP2009185047A (en) * | 2002-09-25 | 2009-08-20 | Daiso Co Ltd | Method for producing glycidylphthalimide |
-
1979
- 1979-04-02 JP JP3994279A patent/JPS6317060B2/ja not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999024393A1 (en) * | 1997-11-07 | 1999-05-20 | Pharmacia & Upjohn Company | Process to produce oxazolidinones |
| EP1772453A1 (en) * | 1997-11-07 | 2007-04-11 | Pharmacia & Upjohn Company LLC | Process to produce Oxazolidinones |
| JP2009185047A (en) * | 2002-09-25 | 2009-08-20 | Daiso Co Ltd | Method for producing glycidylphthalimide |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6317060B2 (en) | 1988-04-12 |
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