GB590645A - Improvements in or relating to the production of 7-hydroxy isoquinoline - Google Patents
Improvements in or relating to the production of 7-hydroxy isoquinolineInfo
- Publication number
- GB590645A GB590645A GB10459/44A GB1045944A GB590645A GB 590645 A GB590645 A GB 590645A GB 10459/44 A GB10459/44 A GB 10459/44A GB 1045944 A GB1045944 A GB 1045944A GB 590645 A GB590645 A GB 590645A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acids
- hydroxyisoquinoline
- salts
- crystallization
- alkali fusion
- 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
- WCRKBMABEPCYII-UHFFFAOYSA-N isoquinolin-7-ol Chemical compound C1=CN=CC2=CC(O)=CC=C21 WCRKBMABEPCYII-UHFFFAOYSA-N 0.000 title abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 3
- 230000004927 fusion Effects 0.000 abstract 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 abstract 2
- 159000000009 barium salts Chemical class 0.000 abstract 2
- 238000002425 crystallisation Methods 0.000 abstract 2
- 230000008025 crystallization Effects 0.000 abstract 2
- 239000012535 impurity Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 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 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- CSNXUYRHPXGSJD-UHFFFAOYSA-N isoquinolin-5-ol Chemical compound N1=CC=C2C(O)=CC=CC2=C1 CSNXUYRHPXGSJD-UHFFFAOYSA-N 0.000 abstract 1
- USPHIQNVSKCZDF-UHFFFAOYSA-N isoquinoline-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=NC=CC2=C1 USPHIQNVSKCZDF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910000000 metal hydroxide Inorganic materials 0.000 abstract 1
- 150000004692 metal hydroxides Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
7-Hydroxyisoquinoline is isolated from mixtures thereof with 5-hydroxyisoquinoline, which are produced by sulphonation of isoquinoline or a sulphate thereof and alkali fusion of the sulphorated material (with or without purification), by preparing a solution of the mixture of isomers in a solvent therefor, e.g. methyl alcohol, and separating the less soluble 7-hydroxyisoquinoline from the solution by fractional crystallization. The sulphonation may be effected by means of sulphuric acid containing an excess (e.g. 15-60 per cent, preferably about 30 per cent) of sulphur trioxide, at 150-250 DEG C. (preferably about 200 DEG C.), advantageously in a pressure vessel. The isoquinolinesulphonic acids are then preferably separated from impurities by reaction with a metal hydroxide or carbonate to form salts which can be purified by crystallization, e.g. the barium salts by the action of barium carbonate (preferred) or hydroxide. The alkali fusion, which may be applied to the acids regenerated from the crystallized salts by acidification, or if desired, to the crude acids, may be effected with sodium or potassium hydroxide, at 200-250 DEG C. The Specification as open to inspection under Sect. 91 comprises also an alternative process in which the barium salts of isoquinoline 7- and 5-sulphonic acids are separated from each other as well as from the impurities, e.g. by crystallization, and the respective acids are liberated, e.g. by the action of sulphuric acid, and subjected separately to alkali fusion, e.g. with potassium hydroxide at 230-240 DEG C. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US590645XA | 1943-08-12 | 1943-08-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB590645A true GB590645A (en) | 1947-07-24 |
Family
ID=22020607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10459/44A Expired GB590645A (en) | 1943-08-12 | 1944-05-31 | Improvements in or relating to the production of 7-hydroxy isoquinoline |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB590645A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114105871A (en) * | 2021-12-06 | 2022-03-01 | 青岛科技大学 | Preparation method of 8-hydroxyquinoline |
-
1944
- 1944-05-31 GB GB10459/44A patent/GB590645A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114105871A (en) * | 2021-12-06 | 2022-03-01 | 青岛科技大学 | Preparation method of 8-hydroxyquinoline |
| CN114105871B (en) * | 2021-12-06 | 2023-11-14 | 青岛科技大学 | Preparation method of 8-hydroxyquinoline |
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