CS263109B1 - Process for preparing 3-amino-4-chlorbenzamide - Google Patents
Process for preparing 3-amino-4-chlorbenzamide Download PDFInfo
- Publication number
- CS263109B1 CS263109B1 CS877397A CS739787A CS263109B1 CS 263109 B1 CS263109 B1 CS 263109B1 CS 877397 A CS877397 A CS 877397A CS 739787 A CS739787 A CS 739787A CS 263109 B1 CS263109 B1 CS 263109B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- amino
- chlorobenzamide
- ncba
- preparing
- chlorbenzamide
- Prior art date
Links
- QHMDKGRWJVOUFU-UHFFFAOYSA-N 3-amino-4-chlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C(N)=C1 QHMDKGRWJVOUFU-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- CGXRJCDXGJRBHV-UHFFFAOYSA-N 4-chloro-3-nitrobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 CGXRJCDXGJRBHV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract 2
- 239000010970 precious metal Substances 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- ZJIRFPOFCZNBAC-UHFFFAOYSA-N 4-amino-2-(2-amino-2-carboxyethyl)sulfanylbutanoic acid Chemical compound NCCC(C(O)=O)SCC(N)C(O)=O ZJIRFPOFCZNBAC-UHFFFAOYSA-N 0.000 description 6
- 108010020212 4-amino-2-(S-cysteinyl)butyric acid Proteins 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DMGFVJVLVZOSOE-UHFFFAOYSA-N 3-amino-4-chlorobenzoic acid Chemical compound NC1=CC(C(O)=O)=CC=C1Cl DMGFVJVLVZOSOE-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 101100004280 Caenorhabditis elegans best-2 gene Proteins 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Způsob přípravy 3-amino-4-chlorbcnzamidu redukcí 3-nitro-4-chlorbenzamidu v organickém rozpouštědle vodíkem, za přítomnosti katalyzátoru na bázi drahých kovů, při teplotě 80 az 120 °C a tlaku 2 až 9 MPa.Process for preparing 3-amino-4-chlorobenzamide reduction of 3-nitro-4-chlorobenzamide v an organic solvent in the presence of hydrogen precious metal catalyst at a temperature of 80 to 120 ° C and a pressure of 2 to 9 MPa.
Description
Vynález se týká způsobu přípravy 3-amino-4-chlorbenzamidu katalytickou redukcí 3-nitro-4-chlorbenzaraidu.The present invention relates to a process for the preparation of 3-amino-4-chlorobenzamide by catalytic reduction of 3-nitro-4-chlorobenzaraid.
Dosud známé způsoby přípravy 3-amíno-4-chlorbenzamidu (dále ACBA) používají redukci 3-nitro-4-chlorbenzamidu (dále NCBA) chloridem zine.čnatým nebo železnými pilinami v prostředí kyseliny sírové· Izolace ACBA z reakční směsi je pracná a vzniká značné množství kapalných^ případně tuhých odpadů.Previously known methods for the preparation of 3-amino-4-chlorobenzamide (hereinafter ACBA) use reduction of 3-nitro-4-chlorobenzamide (hereinafter NCBA) with zinc chloride or iron filings in sulfuric acid environment. the amount of liquid or solid waste.
Nyní byl nalezen způsob přiDravy ACBA redukci NCBA vodíkem za přítomnosti katalyzátoru p/afcíny neko paladfa za tlaku 2 až 5 MPa a teploty 80 až 100 WC. Do autoklávu se předkládá roztok NCBA a katalyzátor.We have now found a process for the preparation of ACBA by reducing NCBA with hydrogen in the presence of a p / afcine non-palladium catalyst at a pressure of 2 to 5 MPa and a temperature of 80 to 100 W C. An NCBA solution and catalyst are introduced into the autoclave.
Vhodným rozpouštědlem Je etanol bu3 96%, nebo bezvodý.Ethanol is either 96% or anhydrous.
Větši obsah vody snižuje rozpustnost jak ACBA, tak hlavně NCBA, a proto je výhodné předkládat sušený NCBA. 2 katalyzátorů se nejlépe osvědčila platina na aktivním uhlí. Reakce probíhá při teplotě 80 až 100 °C a tlaku 2 až 5 MPa. Po skončení reakce a částečném ochlazeni autoklávu je reakční směs přetlačena přes blokový filtr. Oddělený katalyzátor po promytí etanolem se z části vrací do procesu a část jde na regeneraci platiny. Čirý filtrát je zahuštěn na 10 až 30 % průvodního objemu a vyloučené krystaly ACBA se oddělí. Pokud je použit čistý NCBA je možno odpařit etanol k suchu. Získaný produkt však může obsahovat menši množství nečistot.Higher water content reduces the solubility of both ACBA and mainly NCBA, and it is therefore preferable to present dried NCBA. Platinum on activated carbon proved to be the best 2 catalysts. The reaction is carried out at a temperature of 80 to 100 ° C and a pressure of 2 to 5 MPa. After the reaction is complete and the autoclave is partially cooled, the reaction mixture is forced through a block filter. The separated catalyst, after washing with ethanol, partially returns to the process and some goes to the recovery of platinum. The clear filtrate is concentrated to 10-30% of the feed volume and the precipitated ACBA crystals are collected. When pure NCBA is used, ethanol can be evaporated to dryness. However, the product obtained may contain minor impurities.
Přiklad 1Example 1
Do autoklávu bylo předloženo 5 1 96% etanolu, 460 gThe autoclave was charged with 5 L of 96% ethanol, 460 g
NCBA 8 obsahem 102,6 g NOg a 4 g 1% platiny na aktivním uhlí.NCBA 8 contained 102.6 g NOg and 4 g 1% platinum on activated carbon.
263 109263 109
Při intenzivním míchání a teplotě 90 °C byl udržován tlak vodíku na 3 MPa po dobu 8 hodin· Po filtraci katalyzátoru byl filtrát zahuštěn na 0,8 1, vyloučené krystaly odděleny a sušeny· Bylo získáno 279 g produktu s obsahem 93,3 % ACBA a 5,9 % 3-amino-4-chlorbenzoová kyseliny·Under vigorous stirring at 90 ° C, the hydrogen pressure was maintained at 3 MPa for 8 hours. and 5.9% 3-amino-4-chlorobenzoic acid ·
Přiklad 2Example 2
Do autoklávu bylo předloženo 5 1 absolutního etanolu,5 L of absolute ethanol was introduced into the autoclave,
520 g NCBA 8 obsahem 116 g N02 a 1 g 5% platiny na aktivním uhlí· Redukci podle příkladu 1 bylo získáno 310 g produktu s obsahem 94,1 % ACBA a 4,8 % 3-amino-4-chlorbenzoové kyseliny·520 g NCBA 8 containing 116 g NO 2 and 1 g 5% platinum on activated carbon · The reduction according to Example 1 yielded 310 g of a product containing 94.1% ACBA and 4.8% 3-amino-4-chlorobenzoic acid ·
Přiklad 3Example 3
Násada k redukci a postup provedenpe&e přikladu 1· Zahuš těný filtrát byl zředěn 400 ml vody a neutralizován 15% NaOH. Krystaly po promyti vodou byly sušeny, získáno 276 g produktu s obsahem 95,8 % ACBA·Reduction batch and procedure of Example 1 The concentrated filtrate was diluted with 400 mL of water and neutralized with 15% NaOH. The crystals were washed with water and dried, yielding 276 g of product containing 95.8% ACBA ·
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS877397A CS263109B1 (en) | 1987-10-14 | 1987-10-14 | Process for preparing 3-amino-4-chlorbenzamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS877397A CS263109B1 (en) | 1987-10-14 | 1987-10-14 | Process for preparing 3-amino-4-chlorbenzamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS739787A1 CS739787A1 (en) | 1988-08-16 |
| CS263109B1 true CS263109B1 (en) | 1989-04-14 |
Family
ID=5423037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS877397A CS263109B1 (en) | 1987-10-14 | 1987-10-14 | Process for preparing 3-amino-4-chlorbenzamide |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS263109B1 (en) |
-
1987
- 1987-10-14 CS CS877397A patent/CS263109B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS739787A1 (en) | 1988-08-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2542746A (en) | Method of purifying borohydrides of the alkali metals | |
| US4413118A (en) | Process for removal of homogeneous catalyst group VIII metals from process streams | |
| CS263109B1 (en) | Process for preparing 3-amino-4-chlorbenzamide | |
| US3681371A (en) | Process for purification of crude 2-mercaptobenzothiazole | |
| US4061646A (en) | Process for purification of crude 2-mercaptobenzothiazole | |
| US2816136A (en) | Process for the production of alkali and alkaline-earth-metal salts of cyanodithioimidocarbonic acid | |
| US4193938A (en) | Extraction of phenylenediamine from aqueous alkaline solution | |
| Wisian-Neilson et al. | Synthesis of carboxylic acid derivatives of triphenylphosphine cyanoborane | |
| US3842098A (en) | Production of 2-mercaptobenzimidazole by reacting o-phenylene diamine and carbon disulfide | |
| US5510484A (en) | Process for preparing 1,3-dimethy-4,5-diaminouracil | |
| US3703598A (en) | Purification of p-aminophenol | |
| JPS6323179B2 (en) | ||
| US2984661A (en) | Method of preparing pure vitamin b12 and intermediary obtained thereby | |
| EP0418524A2 (en) | Process for preparing amikacin | |
| Ling et al. | CCI.—Crystalline glucose–ammonia and iso glucosamine | |
| KR880002288B1 (en) | Process for the purification of crude 3,4,3',4'-tetraaminodiphenyl | |
| US2219167A (en) | Process for the manufacture of preparations containing the circulatory hormone callicrein | |
| EP0000634A1 (en) | Process for the manufacture of naphthylamine sulphonic acids | |
| US3963770A (en) | Synthesis of ortho-chlorobenzalmalononitrile | |
| US3296290A (en) | Process of separating arsanilic acid | |
| EP0038641B1 (en) | Process for producing d-2-amino-2-(1,4-cyclohexadienyl) acetic acid | |
| US3992506A (en) | Process for recovery of silver and regeneration of 2-mercaptopyridine-1-oxide | |
| US4514380A (en) | Method of preparing tetrarhodium dodecacarbonyl | |
| FI61205C (en) | PROCEDURE FOR THE PURPOSE OF RELEASE TO THE COVER AND FORWARDING OF NICKELS | |
| KR810001349B1 (en) | Preparation method of rifamycin S |