SU815009A1 - Method of producing 5,8-diaminoquinoline - Google Patents
Method of producing 5,8-diaminoquinoline Download PDFInfo
- Publication number
- SU815009A1 SU815009A1 SU782613192A SU2613192A SU815009A1 SU 815009 A1 SU815009 A1 SU 815009A1 SU 782613192 A SU782613192 A SU 782613192A SU 2613192 A SU2613192 A SU 2613192A SU 815009 A1 SU815009 A1 SU 815009A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydrochloric acid
- diaminoquinoline
- nitroquinoline
- producing
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- JYFRBECAJLHOEK-UHFFFAOYSA-N quinoline-5,8-diamine Chemical compound C1=CC=C2C(N)=CC=C(N)C2=N1 JYFRBECAJLHOEK-UHFFFAOYSA-N 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 7
- HUJXJGQTEDKYER-UHFFFAOYSA-N 8-nitroquinolin-5-amine Chemical compound C1=CC=C2C(N)=CC=C([N+]([O-])=O)C2=N1 HUJXJGQTEDKYER-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
- OQHHSGRZCKGLCY-UHFFFAOYSA-N 8-nitroquinoline Chemical compound C1=CN=C2C([N+](=O)[O-])=CC=CC2=C1 OQHHSGRZCKGLCY-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000005010 aminoquinolines Chemical class 0.000 description 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical compound N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000015142 cultured sour cream Nutrition 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- UWPPADMWQVNQFC-UHFFFAOYSA-J tetrachlorostannane;hydrochloride Chemical compound Cl.Cl[Sn](Cl)(Cl)Cl UWPPADMWQVNQFC-UHFFFAOYSA-J 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Изобретение относитс к способу получени 5,8-диаминохинолина, который находит применение в качестве от вердител эпоксидных смол. Известен способ получени 5,8-диа ишнохннолина, к-оторый включает сочетание 5-ам11Нохинолина с фенилдиазони , i)a3деление получаемой смес б- и 8-азопроизводньв 5-%аминохинолйна , восстановление 5-амй«о-8-фенилдиазохйнолина хлористым оловом в сол ной кислоте при кип чении ГЦ. недостатком этого способа вл етс егр слож«ость, св занна с многостадийностыо процесса и использовани ем неустойчивых промежуточных диазосоединений . Цель изобретени - упрощение процееса . Иоставленнай цель достигаетс те что в способе получени 5,8-диаминох нолина 8-нитрохинолин подвергают вза имодействию с сол нокислым гидроксиламином в этаноле в щелочной среде с. последующим восстановлением полученного 5-амино-8-нитрохинолина хлористым оловом в сол ной кислоте. Предлагаемый способ позвол ет иск лючить использование неустойчивых ди зосоединений, исклю ить стадию выделени 5-амино-8-фенилазохинолина из смеси его с изомерньил продуктом. Пример. 5-амино-8-нитрохинс&1ИН. К 5 г (0,03 1-О 8-нитрохинв лина и б г сол нокислого гидроксиламина в 80 мл этилового спирта добавл ют 30 мп 20%-ного спиртового раствора едкого кали . Через 1 ч реакционную массу выпивают в 200 мл воды.Осадок отфильтровывают ,сушат.йлход равен 95%.Т.пл. 280С. 5,8-диаминохинолин. К 4,75 г (,0,025 М) полученного 5амино-8-нитрохинолина в 15 мл 35%-ной сол ной кислоты --добавл ют 20 г крмсталлического хлористого олова в 10 мл 35%-ной сол ной кислоты. Туда же добавл ют 20 МП воды, довод т реакционную смесь до температу кипени и кип т т в течение 1 ч. Затем реакционную массу выливают в 100 мл 20%-иого раствора едкого натра. Выпавший осадок отфильтровывают, сушат. Полученный 5,8-диаминохинолин очищают экстракцией в аппарате Сосклета нонаном t) течение 8 ч. Выпавший из нонана осадок отфильтровывают. Выход основани равен 3,5 г (76%), т.п. . Сметанна проба с веществом, полученным известным способом, не дает депрессии температу1 л плавлени .The invention relates to a process for the preparation of 5,8-diaminoquinoline, which finds use as a version of epoxy resins. A known method for producing 5,8-di-ishchnohnnolina, which includes a combination of 5-am11Noquinoline and phenyldiazonium, i) a3 separating the resulting mixture of b- and 8-azo-5% aminoquinoline, reducing 5-amy "o-8-phenyldiazhoeminol with tin chloride hydrochloric acid at boiling HZ. The disadvantage of this method is the complexity associated with the multistep process and the use of unstable intermediate diazo compounds. The purpose of the invention is to simplify the process. The stated goal is achieved in that in the process of producing 5,8-diamino noline 8-nitroquinoline is subjected to interaction with hydroxylamine hydrochloride in ethanol in an alkaline medium c. the subsequent reduction of the resulting 5-amino-8-nitroquinoline with stannous chloride in hydrochloric acid. The proposed method makes it possible to eliminate the use of unstable dioso compounds, to exclude the stage of isolation of 5-amino-8-phenylazosoquinoline from a mixture of it with the isomeric product. Example. 5-amino-8-nitrohins & To 5 g (0.03 1-O 8-nitroquin line and b g of hydroxylamine hydrochloride in 80 ml of ethyl alcohol were added 30 mp of 20% alcoholic solution of potassium hydroxide. After 1 h, the reaction mass was drunk in 200 ml of water. Precipitate filtered off, dried ylokd is equal to 95%. T. at 280 ° C. 5,8-diaminoquinoline. To 4.75 g (.025 M) of the obtained 5 amino-8-nitroquinoline in 15 ml of 35% hydrochloric acid - add 20 g of crystalline tin chloride in 10 ml of 35% hydrochloric acid are added, 20 MP of water is added thereto, the reaction mixture is brought to the boiling point and boiled for 1 hour. ivayut 100 ml -iogo 20% sodium hydroxide solution. The precipitate was filtered off and dried. The resulting 5,8-diaminohinolin purified by extraction in an apparatus Soskleta nonane t) for 8 hours. The precipitate was filtered off from the precipitate nonane. The base yield is 3.5 g (76%), etc. . Sour cream with a substance obtained in a known manner does not depress the melting point.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782613192A SU815009A1 (en) | 1978-05-04 | 1978-05-04 | Method of producing 5,8-diaminoquinoline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782613192A SU815009A1 (en) | 1978-05-04 | 1978-05-04 | Method of producing 5,8-diaminoquinoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU815009A1 true SU815009A1 (en) | 1981-03-23 |
Family
ID=20763569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782613192A SU815009A1 (en) | 1978-05-04 | 1978-05-04 | Method of producing 5,8-diaminoquinoline |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU815009A1 (en) |
-
1978
- 1978-05-04 SU SU782613192A patent/SU815009A1/en active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5068413A (en) | Process for the preparation of cyclic amino acids and intermediates useful in the process | |
| JPH0249797A (en) | Method for producing erythromycin A oxime and its salts | |
| US4118417A (en) | Process for resolving cis-1-substituted phenyl-1,2-cyclopropanedicarboxylic acids | |
| CN113272275A (en) | Preparation method of levetiracetam intermediate | |
| US3950405A (en) | Trans-4-aminomethylcyclohexane-1-carboxylic acid | |
| US4002666A (en) | Process for the preparation of optically active p-hydroxyphenylglycine | |
| SU815009A1 (en) | Method of producing 5,8-diaminoquinoline | |
| Bailey et al. | The Mannich Reaction with 1, 2-Dibenzoylethane1, 2 | |
| US3007940A (en) | Method of preparing derivatives of 3, 3-pentamethylene-4-hydroxybutyric acid | |
| SU584778A3 (en) | Method of preparing erythromycilamine compounds | |
| SU648080A3 (en) | Method of obtaining 1-tret-butylamino-3-(2,5-dichlorphenoxy)-2-propanol, its salt, racemate or optical antipod | |
| JPS60204750A (en) | Method for preparing DL-β-arylamino acids | |
| SU507225A3 (en) | Production method - propionyl-4-hydroxyproline or its salts | |
| UA70943C2 (en) | A method for obtaining r-(+)-6-carboxamido-3-n-methylamino-1,2,3,4-tetrahydrocarbazole | |
| SU1715803A1 (en) | Method of aminoacid betaines synthesis | |
| SU135081A1 (en) | The method of obtaining 1-trimethylsilylhexin-1-ol-3 | |
| US4254263A (en) | Process for purifying a cyanopyridine compound | |
| SU403675A1 (en) | METHOD OF OBTAINING 2-MERCAPTOIMIDAZOLINE | |
| SU126116A1 (en) | The method of obtaining 5-hydroxytryptophan | |
| US3649628A (en) | Process for producing substituted cyclohexene compounds | |
| SU431156A1 (en) | METHOD OF OBTAINING BIS | |
| US2786849A (en) | Production of 5-(delta-hydroxybutyl) hydantoin | |
| SU447404A1 (en) | Method for preparing 5-nitrofuran-2-hydroxamic acid | |
| SU384818A1 (en) | ||
| SU1310396A1 (en) | Method for producing alkaloids of vitasomnin group |