JPS6366833B2 - - Google Patents

Info

Publication number

JPS6366833B2

JPS6366833B2 JP56028067A JP2806781A JPS6366833B2 JP S6366833 B2 JPS6366833 B2 JP S6366833B2 JP 56028067 A JP56028067 A JP 56028067A JP 2806781 A JP2806781 A JP 2806781A JP S6366833 B2 JPS6366833 B2 JP S6366833B2

Authority

JP

Japan

Prior art keywords

methanol

compound

tosylindole

nitroindole

yield

Prior art date

1981-02-27

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

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• 125000003277 amino group Chemical group 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• 150000002475 indoles Chemical class 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 150000001875 compounds Chemical class 0.000 description 8
• 239000002904 solvent Substances 0.000 description 7
• LAVZKLJDKGRZJG-UHFFFAOYSA-N 4-nitro-1h-indole Chemical compound [O-][N+](=O)C1=CC=CC2=C1C=CN2 LAVZKLJDKGRZJG-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
• 239000000243 solution Substances 0.000 description 5
• POVICWDTCODJQM-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonylindol-4-amine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=CC(N)=C2C=C1 POVICWDTCODJQM-UHFFFAOYSA-N 0.000 description 4
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 4
• 238000004519 manufacturing process Methods 0.000 description 4
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• UUVMVWDDLRKYCB-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonylindol-4-ol Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=CC(O)=C2C=C1 UUVMVWDDLRKYCB-UHFFFAOYSA-N 0.000 description 3
• -1 4-substituted-1-tosylindole Chemical class 0.000 description 3
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 238000006243 chemical reaction Methods 0.000 description 3
• 230000000704 physical effect Effects 0.000 description 3
• 239000000741 silica gel Substances 0.000 description 3
• 229910002027 silica gel Inorganic materials 0.000 description 3
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
• IZJPEYFMAAJLKN-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-nitroindole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=CC([N+]([O-])=O)=C2C=C1 IZJPEYFMAAJLKN-UHFFFAOYSA-N 0.000 description 2
• QBINRHPHFGLNDI-UHFFFAOYSA-N 1-hydroxy-4-nitroindole Chemical group C1=CC=C2N(O)C=CC2=C1[N+]([O-])=O QBINRHPHFGLNDI-UHFFFAOYSA-N 0.000 description 2
• NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical class OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 description 2
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• 238000013375 chromatographic separation Methods 0.000 description 2
• SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 238000000034 method Methods 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 description 2
• 229910000104 sodium hydride Inorganic materials 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 235000010288 sodium nitrite Nutrition 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
• 239000003905 agrochemical Substances 0.000 description 1
• 229930013930 alkaloid Natural products 0.000 description 1
• 125000000217 alkyl group Chemical group 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 229910052736 halogen Inorganic materials 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 229960002508 pindolol Drugs 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
• 238000005406 washing Methods 0.000 description 1