BE517657A - - Google Patents

Info

Publication number

BE517657A

BE517657A BE517657DA BE517657A BE 517657 A BE517657 A BE 517657A BE 517657D A BE517657D A BE 517657DA BE 517657 A BE517657 A BE 517657A

Authority

BE

Belgium

Prior art keywords

hydrazine

isonicotinyl

phenyl

ketone

ethylidene

Prior art date

Links

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• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
• -1 (3 ', 4'-dimethoxyphenyl) -ethylidèn Chemical class 0.000 claims description 11
• 238000000034 method Methods 0.000 claims description 9
• KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
• TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical class OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 8
• 150000002576 ketones Chemical class 0.000 claims description 5
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
• 238000006243 chemical reaction Methods 0.000 claims description 4
• 239000002262 Schiff base Substances 0.000 claims description 3
• 150000004753 Schiff bases Chemical class 0.000 claims description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 3
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• IAANLDLNUKSHBK-UHFFFAOYSA-N C(C1=CC=NC=C1)NN=C1C2=CC=CC=C2C2=C1C=CC=C2 Chemical compound C(C1=CC=NC=C1)NN=C1C2=CC=CC=C2C2=C1C=CC=C2 IAANLDLNUKSHBK-UHFFFAOYSA-N 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
• 150000004983 alkyl aryl ketones Chemical class 0.000 claims 1
• JPWNSMBCNUAXMJ-UHFFFAOYSA-N hexadecylhydrazine Chemical compound CCCCCCCCCCCCCCCCNN JPWNSMBCNUAXMJ-UHFFFAOYSA-N 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 11
• 239000000203 mixture Substances 0.000 description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• 238000001816 cooling Methods 0.000 description 8
• 239000000155 melt Substances 0.000 description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• 238000009835 boiling Methods 0.000 description 6
• 238000002844 melting Methods 0.000 description 6
• 230000008018 melting Effects 0.000 description 6
• 238000001914 filtration Methods 0.000 description 5
• 238000005984 hydrogenation reaction Methods 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• IQZLUWLMQNGTIW-UHFFFAOYSA-N acetoveratrone Chemical compound COC1=CC=C(C(C)=O)C=C1OC IQZLUWLMQNGTIW-UHFFFAOYSA-N 0.000 description 4
• 229910052739 hydrogen Inorganic materials 0.000 description 4
• 239000001257 hydrogen Substances 0.000 description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
• 150000001875 compounds Chemical class 0.000 description 3
• GJLIVZKHVWNESE-UHFFFAOYSA-N 1-(4-methylphenyl)hexadecan-1-one Chemical compound CCCCCCCCCCCCCCCC(=O)C1=CC=C(C)C=C1 GJLIVZKHVWNESE-UHFFFAOYSA-N 0.000 description 2
• DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
• HVCFCNAITDHQFX-UHFFFAOYSA-N 1-cyclopropylethanone Chemical compound CC(=O)C1CC1 HVCFCNAITDHQFX-UHFFFAOYSA-N 0.000 description 2
• UDEVCZRUNOLVLU-UHFFFAOYSA-N 1-phenyloctan-1-one Chemical compound CCCCCCCC(=O)C1=CC=CC=C1 UDEVCZRUNOLVLU-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 2
• YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
• QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
• 229910003446 platinum oxide Inorganic materials 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 description 1
• JPJOOTWNILDNAW-UHFFFAOYSA-N 1-cyclobutylethanone Chemical compound CC(=O)C1CCC1 JPJOOTWNILDNAW-UHFFFAOYSA-N 0.000 description 1
• RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical compound CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 description 1
• QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 description 1
• TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
• WRJZDDJYWWJLIS-UHFFFAOYSA-N 4-methyl-1-phenylpentan-1-one Chemical compound CC(C)CCC(=O)C1=CC=CC=C1 WRJZDDJYWWJLIS-UHFFFAOYSA-N 0.000 description 1
• IWVTZZHXSQKQRU-UHFFFAOYSA-N C(C1=CC=NC=C1)NN=C(C)C1=CC=CC=C1 Chemical compound C(C1=CC=NC=C1)NN=C(C)C1=CC=CC=C1 IWVTZZHXSQKQRU-UHFFFAOYSA-N 0.000 description 1
• UXMQORVHJMUQFD-UHFFFAOYSA-N Heptanophenone Chemical compound CCCCCCC(=O)C1=CC=CC=C1 UXMQORVHJMUQFD-UHFFFAOYSA-N 0.000 description 1
• RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 239000002585 base Substances 0.000 description 1
• 150000001728 carbonyl compounds Chemical class 0.000 description 1
• 239000000470 constituent Substances 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 150000007857 hydrazones Chemical class 0.000 description 1
• 150000002431 hydrogen Chemical class 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 201000008827 tuberculosis Diseases 0.000 description 1