BG106971A - Method for the preparation of 5-cyanophthalide - Google Patents
Method for the preparation of 5-cyanophthalideInfo
- Publication number
- BG106971A BG106971A BG106971A BG10697102A BG106971A BG 106971 A BG106971 A BG 106971A BG 106971 A BG106971 A BG 106971A BG 10697102 A BG10697102 A BG 10697102A BG 106971 A BG106971 A BG 106971A
- Authority
- BG
- Bulgaria
- Prior art keywords
- cyanophthalide
- preparation
- alkyl
- hydrogen
- ring
- Prior art date
Links
- XEEGWTLAFIZLSF-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)OCC2=C1 XEEGWTLAFIZLSF-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229960001653 citalopram Drugs 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 239000002243 precursor Chemical group 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
- 125000003003 spiro group Chemical group 0.000 abstract 1
- JGEUEIOQSKIBAO-UHFFFAOYSA-N thiazonine Chemical group c1cccnsccc1 JGEUEIOQSKIBAO-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
A method for the preparation of 5-cyanophthalide comprising treatment of a compound of formula wherein X is O or S, R1-R2 are each independently selected from hydrogen and C1-6 alkyl, or R1 and R2 together form a C2-5 alkylene chain thereby forming a spiro-ring; R3 is selected from hydrogen and C1-6 alkyl, R4 is selected from hydrogen, C1-6 alkyl, a carboxy group or a precursor group therefore, or R3 and R4 together form a C2-5 alkylene chain thereby forming a spiro ring: with a dehydration agent or alternatively where X is S, thermally cleavage of the thiazonine ring or treatment with a radical initiator, such as peroxide or with light, to form 5-cyanophthalide, which is an important intermediate used in the preparation of the antidepressant drug citalopram. 10 claims
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BG106971A BG65516B1 (en) | 2002-07-31 | 2002-07-31 | Method for the preparation of citalopram |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BG106971A BG65516B1 (en) | 2002-07-31 | 2002-07-31 | Method for the preparation of citalopram |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG106971A true BG106971A (en) | 2003-05-30 |
| BG65516B1 BG65516B1 (en) | 2008-10-31 |
Family
ID=40328096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG106971A BG65516B1 (en) | 2002-07-31 | 2002-07-31 | Method for the preparation of citalopram |
Country Status (1)
| Country | Link |
|---|---|
| BG (1) | BG65516B1 (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US493590A (en) * | 1893-03-14 | James h | ||
| GB8419963D0 (en) * | 1984-08-06 | 1984-09-12 | Lundbeck & Co As H | Intermediate compound and method |
-
2002
- 2002-07-31 BG BG106971A patent/BG65516B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG65516B1 (en) | 2008-10-31 |
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