PL97325B1 - Sposob wytwarzania 3,4-dwuwodoro-1(2h)-ftalazynonu - Google Patents
Sposob wytwarzania 3,4-dwuwodoro-1(2h)-ftalazynonu Download PDFInfo
- Publication number
- PL97325B1 PL97325B1 PL17058174A PL17058174A PL97325B1 PL 97325 B1 PL97325 B1 PL 97325B1 PL 17058174 A PL17058174 A PL 17058174A PL 17058174 A PL17058174 A PL 17058174A PL 97325 B1 PL97325 B1 PL 97325B1
- Authority
- PL
- Poland
- Prior art keywords
- temperature
- acid
- water
- solution
- concentration
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 8
- KCOLJRSQFLZEAB-UHFFFAOYSA-N 3,4-dihydro-2h-phthalazin-1-one Chemical class C1=CC=C2C(=O)NNCC2=C1 KCOLJRSQFLZEAB-UHFFFAOYSA-N 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- -1 alkyl radical Chemical class 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- NKWOXRUJRCMCBH-UHFFFAOYSA-N 1,3-dihydroisoindol-2-amine Chemical compound C1=CC=C2CN(N)CC2=C1 NKWOXRUJRCMCBH-UHFFFAOYSA-N 0.000 description 1
- FACXGJANFZCRTJ-UHFFFAOYSA-N 2,3-diacetyl-4H-phthalazin-1-one Chemical compound C(C)(=O)N1C(C2=CC=CC=C2CN1C(C)=O)=O FACXGJANFZCRTJ-UHFFFAOYSA-N 0.000 description 1
- ZSCSUJZQCNTODA-UHFFFAOYSA-N 2-(bromomethyl)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1CBr ZSCSUJZQCNTODA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2020173 | 1973-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL97325B1 true PL97325B1 (pl) | 1978-02-28 |
Family
ID=10142109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL17058174A PL97325B1 (pl) | 1973-04-27 | 1974-04-25 | Sposob wytwarzania 3,4-dwuwodoro-1(2h)-ftalazynonu |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5013380A (cs) |
| CH (1) | CH580599A5 (cs) |
| CS (1) | CS178916B2 (cs) |
| DD (1) | DD110872A5 (cs) |
| HU (1) | HU167477B (cs) |
| PL (1) | PL97325B1 (cs) |
| SU (1) | SU518128A3 (cs) |
-
1974
- 1974-04-25 CH CH569574A patent/CH580599A5/fr not_active IP Right Cessation
- 1974-04-25 PL PL17058174A patent/PL97325B1/pl unknown
- 1974-04-26 JP JP4745074A patent/JPS5013380A/ja active Pending
- 1974-04-26 HU HULE000745 patent/HU167477B/hu unknown
- 1974-04-26 SU SU2018860A patent/SU518128A3/ru active
- 1974-04-26 CS CS301174A patent/CS178916B2/cs unknown
- 1974-04-26 DD DD17816474A patent/DD110872A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS178916B2 (en) | 1977-10-31 |
| HU167477B (cs) | 1975-10-28 |
| SU518128A3 (ru) | 1976-06-15 |
| JPS5013380A (cs) | 1975-02-12 |
| CH580599A5 (en) | 1976-10-15 |
| DD110872A5 (cs) | 1975-01-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4374987A (en) | Process for the preparation of high purity methotrexate and derivatives thereof | |
| PL164694B1 (pl) | Sposób wytwarzania pochodnych 1 -fenyloimidazolino-2,5-dionu PL PL PL PL PL PL | |
| JPS62187462A (ja) | ５，６−ジアルコキシキナゾリン誘導体 | |
| PL97325B1 (pl) | Sposob wytwarzania 3,4-dwuwodoro-1(2h)-ftalazynonu | |
| US6201121B1 (en) | Process for the preparation of 3-dihalobenzyl-2,4-quinazolinedione derivatives | |
| US4757142A (en) | Process for preparing 6-amino-3-hydrazinopyridazine derivatives | |
| PL185421B1 (pl) | Sposób wytwarzania pochodnych 4-amino-3-okso-2,3,4,5-tetrahydro-1,2,4-triazyny | |
| PL152106B1 (en) | Method of obtaining derivatives of pyrimidine | |
| US3772294A (en) | Process for making pyrazolo-(3,4-d)-pyrimidines | |
| DK170338B1 (da) | Fremgangsmåde til fremstilling af 1,3-dihydro-4-pyridoyl-2H-imidazol-2-oner | |
| EP1065202B1 (en) | 6-(alpha-fluoroalkyl)-4-pyrimidones and process for producing the same | |
| US4057546A (en) | 4-Amino-1,2,4-triazin-5-ones | |
| US3959372A (en) | Glyoxylic acid hydrazide-2-acylhydrazone compounds | |
| US4780542A (en) | Process for the synthesis of esters and amides of carboxylic acids | |
| SU719493A3 (ru) | Способ получени 2-(арилалкилгидразоно)-пропионовой кислоты или ее производных | |
| US4675413A (en) | Process for the preparation of benzimidazole-thiol | |
| Monge‐Vega et al. | Synthesis of some new derivatives of 4‐hydrazino‐5H‐pyridazino [4, 5‐b] indole | |
| JPS5822107B2 (ja) | α↓−アミノメチレン↓−β↓−ホルミルアミノプロピオニトリル及びその製法 | |
| JPH072742A (ja) | ４−アミノ−３−メチル−Ｎ−エチル−Ｎ−（β−ヒドロキシエチル）アニリン硫酸塩の新規製造法 | |
| US4267325A (en) | Bleaching agents | |
| US4255427A (en) | Substituted pyrimido (4,5-c)pyridazines | |
| SU360774A1 (ru) | Способ получения 2 | |
| JPH07247296A (ja) | 有機ゲルマニウム化合物 | |
| PL123691B1 (en) | Process for preparing derivatives of pyrimido/1,2-a/azepines | |
| KR810000802B1 (ko) | 4-벤조일피라졸 유도체 및 그의 금속염의 제조방법 |