DE2527157C2 - Verfahren zur Herstellung von 2-Formylchinoxalin-N↑1↑,N↑4↑-dioxyddimethylacetal - Google Patents
Verfahren zur Herstellung von 2-Formylchinoxalin-N↑1↑,N↑4↑-dioxyddimethylacetalInfo
- Publication number
- DE2527157C2 DE2527157C2 DE19752527157 DE2527157A DE2527157C2 DE 2527157 C2 DE2527157 C2 DE 2527157C2 DE 19752527157 DE19752527157 DE 19752527157 DE 2527157 A DE2527157 A DE 2527157A DE 2527157 C2 DE2527157 C2 DE 2527157C2
- Authority
- DE
- Germany
- Prior art keywords
- formylquinoxaline
- reaction
- dioxyddimethylacetal
- benzofuroxan
- solvent
- 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
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 6
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 title description 4
- OKEAMBAZBICIFP-UHFFFAOYSA-N 3-oxido-2,1,3-benzoxadiazol-3-ium Chemical compound C1=CC=CC2=[N+]([O-])ON=C21 OKEAMBAZBICIFP-UHFFFAOYSA-N 0.000 claims description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- DWJDEJZHYRTMRR-UHFFFAOYSA-N 2,2-dimethoxypropanal Chemical compound COC(C)(OC)C=O DWJDEJZHYRTMRR-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000000908 ammonium hydroxide Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000004036 acetal group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- -1 pyrrolidine Chemical class 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE002247 HU169049B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-06-18 | 1974-06-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2527157A1 DE2527157A1 (de) | 1976-02-05 |
| DE2527157C2 true DE2527157C2 (de) | 1984-01-12 |
Family
ID=10995562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752527157 Expired DE2527157C2 (de) | 1974-06-18 | 1975-06-18 | Verfahren zur Herstellung von 2-Formylchinoxalin-N↑1↑,N↑4↑-dioxyddimethylacetal |
Country Status (7)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5613099A (en) * | 1979-07-10 | 1981-02-07 | Nichireki Chem Ind Co Ltd | Treating method of sludge |
| JPS63240999A (ja) * | 1987-03-30 | 1988-10-06 | Ebara Infilco Co Ltd | 有機性汚泥の脱水方法 |
| JPS63258607A (ja) * | 1987-04-17 | 1988-10-26 | Ebara Infilco Co Ltd | 凝集剤 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670693C3 (de) * | 1966-05-04 | 1975-10-16 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Chinoxalin-di-N-oxiden |
| GB1134729A (en) * | 1966-11-08 | 1968-11-27 | Research Corp | Quinoxaline-di-n-oxides |
| GB1308370A (en) * | 1969-12-09 | 1973-02-21 | Research Corp | 1-hydroxy-3-oxo-benzimidazoles quinoxaline-di-n-oxides and benzimidazole-mono-and di-n-oxides |
-
1974
- 1974-06-18 HU HUEE002247 patent/HU169049B/hu unknown
-
1975
- 1975-05-23 GB GB2254375A patent/GB1490589A/en not_active Expired
- 1975-06-16 SE SE7506899A patent/SE419545B/xx not_active IP Right Cessation
- 1975-06-17 SU SU752145959A patent/SU650504A3/ru active
- 1975-06-18 JP JP7326675A patent/JPS5123276A/ja active Granted
- 1975-06-18 DE DE19752527157 patent/DE2527157C2/de not_active Expired
- 1975-06-18 DK DK275475A patent/DK137798B/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5123276A (en) | 1976-02-24 |
| SE7506899L (sv) | 1975-12-19 |
| DE2527157A1 (de) | 1976-02-05 |
| SU650504A3 (ru) | 1979-02-28 |
| DK137798B (da) | 1978-05-08 |
| DK137798C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-10-09 |
| JPS56430B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-01-08 |
| GB1490589A (en) | 1977-11-02 |
| DK275475A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-12-19 |
| SE419545B (sv) | 1981-08-10 |
| HU169049B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |