CH630602A5 - Process for the preparation of N-(3,4-dimethylphenyl)-D-ribamine - Google Patents
Process for the preparation of N-(3,4-dimethylphenyl)-D-ribamine Download PDFInfo
- Publication number
- CH630602A5 CH630602A5 CH1336377A CH1336377A CH630602A5 CH 630602 A5 CH630602 A5 CH 630602A5 CH 1336377 A CH1336377 A CH 1336377A CH 1336377 A CH1336377 A CH 1336377A CH 630602 A5 CH630602 A5 CH 630602A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethylphenyl
- ribamine
- lactone
- ribonic acid
- hydrogenation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims description 13
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 7
- HFZKOYWDLDYELC-UHFFFAOYSA-N 1,2-dimethyl-4-nitrobenzene Chemical class CC1=CC=C([N+]([O-])=O)C=C1C HFZKOYWDLDYELC-UHFFFAOYSA-N 0.000 claims description 6
- 239000005751 Copper oxide Substances 0.000 claims description 6
- 229910000431 copper oxide Inorganic materials 0.000 claims description 6
- -1 hydrazo Chemical group 0.000 claims description 6
- WEVSWJHEFVKUSR-UHFFFAOYSA-N bis(3,4-dimethylphenyl)diazene Chemical compound C1=C(C)C(C)=CC=C1N=NC1=CC=C(C)C(C)=C1 WEVSWJHEFVKUSR-UHFFFAOYSA-N 0.000 claims description 5
- NVDICYFEQBBCOH-UHFFFAOYSA-N (3,4-dimethylphenyl)-(3,4-dimethylphenyl)imino-oxidoazanium Chemical compound C1=C(C)C(C)=CC=C1N=[N+]([O-])C1=CC=C(C)C(C)=C1 NVDICYFEQBBCOH-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical class CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical compound CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- QXKAIJAYHKCRRA-BXXZVTAOSA-N D-ribonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O QXKAIJAYHKCRRA-BXXZVTAOSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QNRFMBRRBOYLJH-IJLUTSLNSA-N (2r,3r,4r)-n-(3,4-dimethylphenyl)-2,3,4,5-tetrahydroxypentanamide Chemical compound CC1=CC=C(NC(=O)[C@H](O)[C@H](O)[C@H](O)CO)C=C1C QNRFMBRRBOYLJH-IJLUTSLNSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- FWXNGZXYKWNRQM-UHFFFAOYSA-N 1,2-bis(3,4-dimethylphenyl)hydrazine Chemical compound C1=C(C)C(C)=CC=C1NNC1=CC=C(C)C(C)=C1 FWXNGZXYKWNRQM-UHFFFAOYSA-N 0.000 description 1
- BIJJCIFZOOLNRN-UHFFFAOYSA-N 1,2-dimethyl-4-nitrosobenzene Chemical compound CC1=CC=C(N=O)C=C1C BIJJCIFZOOLNRN-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229930003471 Vitamin B2 Natural products 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PURJYVIHCDBIRA-UHFFFAOYSA-N [Cu]=O.[O-2].[Al+3].[O-2].[O-2].[Al+3] Chemical compound [Cu]=O.[O-2].[Al+3].[O-2].[O-2].[Al+3] PURJYVIHCDBIRA-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- OMQHMQCZNLHYAG-UHFFFAOYSA-N n-(3,4-dimethylphenyl)hydroxylamine Chemical group CC1=CC=C(NO)C=C1C OMQHMQCZNLHYAG-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000009419 refurbishment Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000011716 vitamin B2 Substances 0.000 description 1
- 235000019164 vitamin B2 Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762650830 DE2650830A1 (de) | 1976-11-06 | 1976-11-06 | Verfahren zur herstellung von n- eckige klammer auf 3,4-dimethylphenyl eckige klammer zu -d-ribamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH630602A5 true CH630602A5 (en) | 1982-06-30 |
Family
ID=5992572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1336377A CH630602A5 (en) | 1976-11-06 | 1977-11-02 | Process for the preparation of N-(3,4-dimethylphenyl)-D-ribamine |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5359632A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1101887A (cg-RX-API-DMAC10.html) |
| CH (1) | CH630602A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2650830A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2370033A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1586677A (cg-RX-API-DMAC10.html) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL60827C (cg-RX-API-DMAC10.html) * | 1944-12-15 | |||
| DE2558515C3 (de) * | 1975-12-24 | 1979-02-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von N- [3,4-Dimethylphenyl] D-ribamin |
| FR2336377A1 (fr) * | 1975-12-24 | 1977-07-22 | Basf Ag | Procede de preparation de la n-(3,4-dimethylphenyl)-d-ribamine |
-
1976
- 1976-11-06 DE DE19762650830 patent/DE2650830A1/de not_active Withdrawn
-
1977
- 1977-10-11 CA CA288,684A patent/CA1101887A/en not_active Expired
- 1977-10-31 JP JP12978977A patent/JPS5359632A/ja active Pending
- 1977-11-02 CH CH1336377A patent/CH630602A5/de not_active IP Right Cessation
- 1977-11-03 FR FR7732982A patent/FR2370033A1/fr active Granted
- 1977-11-04 GB GB45920/77A patent/GB1586677A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1101887A (en) | 1981-05-26 |
| FR2370033A1 (fr) | 1978-06-02 |
| JPS5359632A (en) | 1978-05-29 |
| GB1586677A (en) | 1981-03-25 |
| FR2370033B1 (cg-RX-API-DMAC10.html) | 1981-12-18 |
| DE2650830A1 (de) | 1978-05-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |