BE569929A - - Google Patents

Info

Publication number

BE569929A

BE569929A BE569929DA BE569929A BE 569929 A BE569929 A BE 569929A BE 569929D A BE569929D A BE 569929DA BE 569929 A BE569929 A BE 569929A

Authority

BE

Belgium

Prior art keywords

alkyl

substituted

derivatives

pyridinaldehydes

pyridine

Prior art date

Links

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• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
• 238000000034 method Methods 0.000 claims description 9
• CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical class O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 150000002989 phenols Chemical class 0.000 claims description 8
• 238000002360 preparation method Methods 0.000 claims description 8
• 238000003756 stirring Methods 0.000 claims description 8
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 238000006243 chemical reaction Methods 0.000 claims description 4
• 238000001816 cooling Methods 0.000 claims description 4
• 239000013078 crystal Substances 0.000 claims description 3
• 239000007858 starting material Substances 0.000 claims description 3
• LJROKJGQSPMTKB-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-pyridin-2-ylmethyl]phenol Chemical class C1=CC(O)=CC=C1C(C=1N=CC=CC=1)C1=CC=C(O)C=C1 LJROKJGQSPMTKB-UHFFFAOYSA-N 0.000 claims description 2
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
• 229910052739 hydrogen Inorganic materials 0.000 claims description 2
• 239000001257 hydrogen Substances 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
• 150000003222 pyridines Chemical class 0.000 claims description 2
• OIKGFMHISSQNRL-UHFFFAOYSA-N N-[(6-methylpyridin-2-yl)methylidene]hydroxylamine Chemical compound CC1=CC=CC(C=NO)=N1 OIKGFMHISSQNRL-UHFFFAOYSA-N 0.000 claims 1
• 238000002425 crystallisation Methods 0.000 claims 1
• 230000008025 crystallization Effects 0.000 claims 1
• 238000009833 condensation Methods 0.000 description 6
• 230000005494 condensation Effects 0.000 description 6
• 239000000203 mixture Substances 0.000 description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• 150000001875 compounds Chemical class 0.000 description 4
• 238000001953 recrystallisation Methods 0.000 description 4
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 3
• 150000001299 aldehydes Chemical class 0.000 description 3
• 239000012043 crude product Substances 0.000 description 3
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
• 239000000155 melt Substances 0.000 description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
• -1 pyridyl ketones Chemical class 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• IOVVDRDEXYHYNT-UHFFFAOYSA-N (pyridin-2-ylmethylideneamino)urea Chemical compound NC(=O)NN=CC1=CC=CC=N1 IOVVDRDEXYHYNT-UHFFFAOYSA-N 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
• 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
• 230000021736 acetylation Effects 0.000 description 1
• 238000006640 acetylation reaction Methods 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• MTFJSAGADRTKCI-VMPITWQZSA-N chembl77510 Chemical compound O\N=C\C1=CC=CC=N1 MTFJSAGADRTKCI-VMPITWQZSA-N 0.000 description 1
• 238000003776 cleavage reaction Methods 0.000 description 1
• 239000007859 condensation product Substances 0.000 description 1
• 239000000470 constituent Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 239000008141 laxative Substances 0.000 description 1
• 229940125722 laxative agent Drugs 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
• 230000007935 neutral effect Effects 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1