JPH0466223B2 - - Google Patents
Info
- Publication number
- JPH0466223B2 JPH0466223B2 JP59052952A JP5295284A JPH0466223B2 JP H0466223 B2 JPH0466223 B2 JP H0466223B2 JP 59052952 A JP59052952 A JP 59052952A JP 5295284 A JP5295284 A JP 5295284A JP H0466223 B2 JPH0466223 B2 JP H0466223B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- halogenated
- dichloro
- formula
- nitrobenzoic 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 - Lifetime
Links
- 150000005181 nitrobenzenes Chemical class 0.000 claims description 10
- 150000005338 nitrobenzoic acids Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000006114 decarboxylation reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- -1 2,3,4-trichloro-6-nitrobenzoic acid Chemical compound 0.000 description 8
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 8
- 125000001153 fluoro group Chemical class F* 0.000 description 5
- JSEVUBOYVADSHX-UHFFFAOYSA-N 1,3-dichloro-2-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(F)=C1Cl JSEVUBOYVADSHX-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 235000003270 potassium fluoride Nutrition 0.000 description 4
- 239000011698 potassium fluoride Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MTBYTWZDRVOMBR-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl MTBYTWZDRVOMBR-UHFFFAOYSA-N 0.000 description 1
- BGKIECJVXXHLDP-UHFFFAOYSA-N 1,2,3-trichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1Cl BGKIECJVXXHLDP-UHFFFAOYSA-N 0.000 description 1
- HHLCSFGOTLUREE-UHFFFAOYSA-N 1,2,3-trichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C(Cl)=C1 HHLCSFGOTLUREE-UHFFFAOYSA-N 0.000 description 1
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
- NTBYINQTYWZXLH-UHFFFAOYSA-N 1,2-dichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1 NTBYINQTYWZXLH-UHFFFAOYSA-N 0.000 description 1
- OWALCRQILZGQDH-UHFFFAOYSA-N 1,3-dichloro-2,4-difluoro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(F)C(Cl)=C1F OWALCRQILZGQDH-UHFFFAOYSA-N 0.000 description 1
- YJUUZFWMKJBVFJ-UHFFFAOYSA-N 1,3-dimethylimidazolidin-4-one Chemical compound CN1CN(C)C(=O)C1 YJUUZFWMKJBVFJ-UHFFFAOYSA-N 0.000 description 1
- XNJAYQHWXYJBBD-UHFFFAOYSA-N 1,4-difluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1F XNJAYQHWXYJBBD-UHFFFAOYSA-N 0.000 description 1
- QUIMTLZDMCNYGY-UHFFFAOYSA-N 2,4-dichloro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1Cl QUIMTLZDMCNYGY-UHFFFAOYSA-N 0.000 description 1
- RJXOVESYJFXCGI-UHFFFAOYSA-N 2,4-difluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1F RJXOVESYJFXCGI-UHFFFAOYSA-N 0.000 description 1
- DPHCXXYPSYMICK-UHFFFAOYSA-N 2-chloro-1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(Cl)=C1 DPHCXXYPSYMICK-UHFFFAOYSA-N 0.000 description 1
- KSLPTAKLPKUBES-UHFFFAOYSA-N 3,4,5-trichloro-2-nitrobenzoic acid Chemical compound ClC=1C(=C(C(=C(C(=O)O)C1)[N+](=O)[O-])Cl)Cl KSLPTAKLPKUBES-UHFFFAOYSA-N 0.000 description 1
- ZWJZUUYLXVXJSF-UHFFFAOYSA-N 3,4-dichloro-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(Cl)=C1[N+]([O-])=O ZWJZUUYLXVXJSF-UHFFFAOYSA-N 0.000 description 1
- LKMJMYZOEGSMDN-UHFFFAOYSA-N 3,5-dichloro-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC(Cl)=C1[N+]([O-])=O LKMJMYZOEGSMDN-UHFFFAOYSA-N 0.000 description 1
- ZBEWIPTYUHHZIS-UHFFFAOYSA-N 3,5-difluoro-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC(F)=CC(F)=C1[N+]([O-])=O ZBEWIPTYUHHZIS-UHFFFAOYSA-N 0.000 description 1
- TVKAWNFBYDPGGW-UHFFFAOYSA-N 3,6-difluoro-2-nitrobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC(F)=C1[N+]([O-])=O TVKAWNFBYDPGGW-UHFFFAOYSA-N 0.000 description 1
- SUHYJVCHLDIPIY-UHFFFAOYSA-N 4,5-dichloro-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O SUHYJVCHLDIPIY-UHFFFAOYSA-N 0.000 description 1
- QWRNVDWDFCINEY-UHFFFAOYSA-N 4-bromo-2-chloro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1Cl QWRNVDWDFCINEY-UHFFFAOYSA-N 0.000 description 1
- GGTQVIUWLUDQKR-UHFFFAOYSA-N 4-chloro-5-fluoro-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(Cl)C=C1[N+]([O-])=O GGTQVIUWLUDQKR-UHFFFAOYSA-N 0.000 description 1
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- MOVBJUGHBJJKOW-UHFFFAOYSA-N methyl 2-amino-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1N MOVBJUGHBJJKOW-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59052952A JPS60197640A (ja) | 1984-03-19 | 1984-03-19 | ハロゲン化ニトロベンゼン類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59052952A JPS60197640A (ja) | 1984-03-19 | 1984-03-19 | ハロゲン化ニトロベンゼン類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60197640A JPS60197640A (ja) | 1985-10-07 |
| JPH0466223B2 true JPH0466223B2 (cs) | 1992-10-22 |
Family
ID=12929211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59052952A Granted JPS60197640A (ja) | 1984-03-19 | 1984-03-19 | ハロゲン化ニトロベンゼン類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60197640A (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3055504A1 (en) * | 2017-03-14 | 2018-09-20 | Daiichi Sankyo Company, Limited | Method for producing 3,6-disubstituted imidazo[1,2-b]pyridazine derivative |
| CN109467509B (zh) * | 2017-09-08 | 2021-09-24 | 联化科技股份有限公司 | 一种取代硝基苯类化合物的制备方法 |
-
1984
- 1984-03-19 JP JP59052952A patent/JPS60197640A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60197640A (ja) | 1985-10-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6251260B2 (cs) | ||
| JP4872668B2 (ja) | ２−アミノ−５−ヨード安息香酸の製造方法 | |
| HU193589B (en) | Process for preparing fluorinated phtaloyl- and terephtaloyl compounds | |
| JPH03161462A (ja) | ３，４，６―トリフルオロフタル酸無水物の脱炭酸による２，４，５―トリフルオロ安息香酸の調製 | |
| JPH0466223B2 (cs) | ||
| JPS5925779B2 (ja) | 立体異性脂環ジアミンの異性化法 | |
| JPS61257938A (ja) | ｍ−フエノキシベンジルアルコ−ルの製造方法 | |
| JPH024580B2 (cs) | ||
| US5003103A (en) | Preparation of 2-choloro-4,5-difluorobenzoic acid from 4,5-difluorophthalic anhydride of 4,5-difluorophthalic acid | |
| EP0274194B1 (en) | Process for the preparation of 2-nitro-5-phenoxy-n-alkylsulfonyl benzamides by nitration | |
| JPH0466225B2 (cs) | ||
| JP3814742B2 (ja) | ４−フルオロサリチル酸類 | |
| JPH0616613A (ja) | ２−クロル−４，５−ジフルオルベンゾニトリル及び その製法 | |
| JPH0258253B2 (cs) | ||
| EP0655997B1 (en) | Pyridinium intermediates and the process for preparing the same | |
| US4994606A (en) | Process for the preparation of 4,5-difluoroanthranilic acid from 4,5-difluorophthalic anhydride or 4,5-difluorophthalic acid | |
| US5233085A (en) | Preparation of 2,4,5-trifluorobenzoic acid by decarboxylation of 3,4,6-trifluorophthalic acid | |
| CN109081826B (zh) | 氧化剂ibx的制备方法 | |
| JP3403466B2 (ja) | ２，５−ジメトキシ−４，４′，４″−トリニトロトリフェニルアミンの製造法 | |
| JPS6056157B2 (ja) | 高純度ハロゲンナフタル酸無水物の製法 | |
| JPH069509A (ja) | オルト−ハロゲノニトロベンゼンの選択的脱ハロゲン化方法 | |
| JPH072690B2 (ja) | ３−メチル−４−ニトロフエノ−ルの製造方法 | |
| JP3500504B2 (ja) | ２−ヒドロキシカルバゾールの製造方法 | |
| JPS60237051A (ja) | ２−フルオロニトロベンゼン誘導体の製造方法 | |
| JPH03178950A (ja) | ３，４―ジフルオロニトロベンゼンの製造方法およびその中間体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |