SU108811A1 - The method of obtaining 5-nitro-4-amino-1-naphthol - Google Patents
The method of obtaining 5-nitro-4-amino-1-naphtholInfo
- Publication number
- SU108811A1 SU108811A1 SU565227A SU565227A SU108811A1 SU 108811 A1 SU108811 A1 SU 108811A1 SU 565227 A SU565227 A SU 565227A SU 565227 A SU565227 A SU 565227A SU 108811 A1 SU108811 A1 SU 108811A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- nitro
- naphthol
- amino
- obtaining
- nitroso
- Prior art date
Links
- UNXWKVZPLBVYIT-UHFFFAOYSA-N 4-amino-5-nitronaphthalen-1-ol Chemical compound C1=CC([N+]([O-])=O)=C2C(N)=CC=C(O)C2=C1 UNXWKVZPLBVYIT-UHFFFAOYSA-N 0.000 title description 3
- 238000000034 method Methods 0.000 title description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- DJYUBITZUIZUJH-UHFFFAOYSA-N 5-nitro-4-nitrosonaphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=C(N=O)C2=C1[N+]([O-])=O DJYUBITZUIZUJH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ARBFKKLBTARDKA-UHFFFAOYSA-N 1,4-dioxin-2-amine Chemical compound NC1=COC=CO1 ARBFKKLBTARDKA-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
5-ни1 ри-4-нагрозо-1-наф|Ол до сего времени не удавалось подвергнуть частичному восстановлению. При восстановлении его металлическим или хлористым оловом в сол ной кислоте были получены лишь продукт иолиого восстановлени -4 ,5-д11амино-1-нафтол и продукт его дальнейшего нревраш;ени --5-амино-1 ,4-диоксин афта ЛИН.5-ni1 ri-4-agroso-1-naph | Ol has not yet been able to undergo partial restoration. When it was reduced by metal or tin chloride in hydrochloric acid, only the product of molar reduction -4, 5-d11amino-1-naphthol and the product of its further Nrevrash were obtained; it was 5-amino-1, 4-dioxin apha LIN.
Установлеио, что если примен ть фенилгидразин в качестве восстановител и вести процесс в среде органического растворител , например , в бензоле или спирте, то представл етс возмоукным осу ,ествить и частичное восстановление . 5-нитро-4-нитрозо-1-нафтола, при котором первоначально восстанавливаетс нитрозогруипа. В результате получаетс ранее неизвестный 5-нитро-4-амино-1-нафтол, который может найти г.рименение как промежуточный продукт дл синтеза красителей.It has been found that if phenylhydrazine is used as a reducing agent and the process is carried out in an organic solvent medium, for example benzene or alcohol, it is possible that it can be partially reduced. 5-nitro-4-nitroso-1-naphthol, in which the nitrosogruip is initially reduced. The result is a previously unknown 5-nitro-4-amino-1-naphthol, which may find application as an intermediate for the synthesis of dyes.
Пример 2,18 г 5-нитро-4-нитрозо-1-нафгола нагревают с 2,22 г фенилгидразина и 25 мл этилового спирта на вод ной бане до кипени в течение двух часов. По охлаждени реакщгжную массу фильтруют и осадок прэ.мываютExample 2.18 g of 5-nitro-4-nitroso-1-naphgol is heated to 2.22 g of phenylhydrazine and 25 ml of ethyl alcohol in a water bath to boil for two hours. After cooling, the reactive mass is filtered and the precipitate is washed.
эфиром (нерастворимы в эфире осадок-непрореагировавший 5-нитро4-нитрозо-1-нафтол , 0,34 г). Из фильтрата при отгонке большей части растворител получают осадок 5-нитро-4-а.мино-1-нафтола (1,02 г). Выход, счита на вступивший в реакцию о-нитро-4-нитрозо1-нафтол , рйвен 59,396.ether (insoluble in ether precipitate-unreacted 5-nitro4-nitroso-1-naphthol, 0.34 g). A precipitate of 5-nitro-4-a.mino-1-naphthol (1.02 g) is obtained from the filtrate by distilling off most of the solvent. The output, counting on entered into the reaction of o-nitro-4-nitroso-naphtol, raven 59,396.
Кристаллизацией из смеси ацетона с бензолом получают желтый кристаллический осадок (под микроскопом желтые призмы).Crystallization from a mixture of acetone and benzene gives a yellow crystalline precipitate (yellow prisms under the microscope).
Найдено: % С-58,4; 58,6.Found:% C-58.4; 58.6.
%Н-4,0; 4,1. CjoHsOgN., Вычислено: %С-58,«0. %Н-3,9.% H-4.0; 4.1. CjoHsOgN., Calculated:% C-58, “0. % H-3.9.
При действии газообразного хлористого водорода на эфирный раствор 5-нитро-4-амино-1-нафтола на холоде получают соответствуюш ,ий хлоргидрат. Кристаллизацией из этилового спирта с последуюш ,им насыш,ением хлористым водородом получают лселтый порошок (под микроскопом желтые пластинки ).Under the action of gaseous hydrogen chloride on the ethereal solution of 5-nitro-4-amino-1-naphthol in the cold, the corresponding hydrochloride is obtained. Crystallization from ethyl alcohol followed by saturation with hydrogen chloride gives the powder to the powder (yellow plates under the microscope).
Найдено: %С-50,0; 50,1. %Н-3,9; 3,8. ,7; 11,8. CioHgOoNoClFound:% C-50.0; 50.1. % H-3.9; 3.8. , 7; 11.8. CioHgOoNoCl
С-49,9. ,,7.C-49.9. ,, 7.
Вычислено: 96N-11,6. При действии смеси уксусного ангидрида с уксусной кпслоюй на 5-нитро-4-ами1Ю-1-иафтол на холоде получают моно-М-ацстильног производное. Перекристаллпзацией из разбавленного этилового спирта получают желтые иголочки, образующие пучки; темп. пл.- 220-221 с разложениел. Предмет изобретени Снособ получени о-нитро-4-амино-1-нлфтола , о т л и ч а ю щ и и с тем, что o-HHTpo-l-HMTpoao-l-Haqbтол обрабатывают фенилгидразином в с{1еде ( /ганического раствор тел , например, сиирта или бензола. Calculated: 96N-11.6. Under the action of a mixture of acetic anhydride and acetic acid on 5-nitro-4-ami1U-1-yaftol, in the cold, a mono-M-styillog derivative is obtained. By recrystallization from diluted ethyl alcohol, yellow needles are obtained, forming bunches; pace. Sq.-220-221 with decomposition. The subject of the invention is a method for the preparation of o-nitro-4-amino-1-nl-phthol, one that is o-HHTpo-1-HM a solution of solids, for example, syirt or benzene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU565227A SU108811A1 (en) | 1957-01-23 | 1957-01-23 | The method of obtaining 5-nitro-4-amino-1-naphthol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU565227A SU108811A1 (en) | 1957-01-23 | 1957-01-23 | The method of obtaining 5-nitro-4-amino-1-naphthol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU108811A1 true SU108811A1 (en) | 1957-11-30 |
Family
ID=48381888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU565227A SU108811A1 (en) | 1957-01-23 | 1957-01-23 | The method of obtaining 5-nitro-4-amino-1-naphthol |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU108811A1 (en) |
-
1957
- 1957-01-23 SU SU565227A patent/SU108811A1/en active
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