JPH0116825B2 - - Google Patents
Info
- Publication number
- JPH0116825B2 JPH0116825B2 JP9554681A JP9554681A JPH0116825B2 JP H0116825 B2 JPH0116825 B2 JP H0116825B2 JP 9554681 A JP9554681 A JP 9554681A JP 9554681 A JP9554681 A JP 9554681A JP H0116825 B2 JPH0116825 B2 JP H0116825B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- chloro
- hydroxy
- acid
- acetic acid
- 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
- -1 3-chloro-4-hydroxy-5-aminophenyl acetic acid Chemical compound 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 7
- FLJCUXHZDXQIHH-UHFFFAOYSA-N 2-(3-chloro-5-cyano-4-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC(Cl)=C(O)C(C#N)=C1 FLJCUXHZDXQIHH-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical group [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 150000001243 acetic acids Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000006193 diazotization reaction Methods 0.000 description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012450 pharmaceutical intermediate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XUSKZLBLGHBCLD-UHFFFAOYSA-N 2-(3-aminophenyl)acetic acid Chemical compound NC1=CC=CC(CC(O)=O)=C1 XUSKZLBLGHBCLD-UHFFFAOYSA-N 0.000 description 1
- YIXNAWHSUSDQPW-UHFFFAOYSA-N 2-(3-cyanophenyl)-2-hydroxyacetic acid Chemical class OC(=O)C(O)C1=CC=CC(C#N)=C1 YIXNAWHSUSDQPW-UHFFFAOYSA-N 0.000 description 1
- DKFPBXQCCCIWLC-UHFFFAOYSA-N 2-cyano-2-phenylacetic acid Chemical compound OC(=O)C(C#N)C1=CC=CC=C1 DKFPBXQCCCIWLC-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- NLEUXPOVZGDKJI-UHFFFAOYSA-N nickel(2+);dicyanide Chemical compound [Ni+2].N#[C-].N#[C-] NLEUXPOVZGDKJI-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9554681A JPS57209262A (en) | 1981-06-19 | 1981-06-19 | 3-chloro-4-hydroxy-5-cyanophenylacetic acid and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9554681A JPS57209262A (en) | 1981-06-19 | 1981-06-19 | 3-chloro-4-hydroxy-5-cyanophenylacetic acid and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57209262A JPS57209262A (en) | 1982-12-22 |
| JPH0116825B2 true JPH0116825B2 (zh) | 1989-03-27 |
Family
ID=14140561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9554681A Granted JPS57209262A (en) | 1981-06-19 | 1981-06-19 | 3-chloro-4-hydroxy-5-cyanophenylacetic acid and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57209262A (zh) |
-
1981
- 1981-06-19 JP JP9554681A patent/JPS57209262A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57209262A (en) | 1982-12-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6345254A (ja) | アルデヒト官能基を有するカルバゾ−ルおよびその製造方法 | |
| EP0036636B1 (en) | A method and intermediates for preparing 3,3'-azo-bis-(6-hydroxy benzoic acid) | |
| JPH0116825B2 (zh) | ||
| JP2571950B2 (ja) | シクロペンテノン誘導体及びその製造法 | |
| JPS6332796B2 (zh) | ||
| JPS5811867B2 (ja) | ５，５−ジメチル−４−フエニルオキサゾリジン−２−オン誘導体の製造方法 | |
| JP3303050B2 (ja) | アゾニアアダマンタン化合物およびこのものからのアザアダマンタン化合物の製造方法並びに該アゾニアアダマンタン化合物の製造方法 | |
| JP3357570B2 (ja) | ３−置換−１−プロパノールの製造方法 | |
| CN108484495B (zh) | 一种3-溴-7-羟基喹啉的合成方法 | |
| JPS6122081A (ja) | ヒダントイン化合物の製造法 | |
| JPH0131516B2 (zh) | ||
| JPS6053021B2 (ja) | ヒダントインの製造法 | |
| US5475140A (en) | Process for producing N,N-disubstituted p-phenylenediamine derivative sulfate | |
| US5266704A (en) | Process for production of 2-substituted-4-hydromethylimidazole compounds | |
| JP4105821B2 (ja) | ジアゾ化合物 | |
| RU2026857C1 (ru) | Способ получения 2-метоксиизобутилизоцианида | |
| CN117069611A (zh) | 一种1-(2,4,6-三氯苯基)丙-2-酮o-甲基肟的制备方法 | |
| JPH0578544B2 (zh) | ||
| JP2515122B2 (ja) | アントラニル酸エステルの製造方法 | |
| Sugasawa et al. | Synthesis in the Benzoquinolizine Group. XXIII.: Synthesis of rac-C-bisnoremetine. | |
| JPS61165351A (ja) | オキシフエニルマロン酸半エステルの製造法 | |
| Karady et al. | Synthesis of L-. alpha.-(3, 4-dihydroxybenzyl)-. alpha.-hydrazinopropionic acid from optically active precursors by N-homologization | |
| JPS5967252A (ja) | 光学活性β−アミノイソ酪酸及びその誘導体の製造法 | |
| JPS609703B2 (ja) | 光学活性ベンジルアルコール誘導体の製法 | |
| JPS6323981B2 (zh) |