DE2257710C3 - Verfahren zur Herstellung N-substituierter Indole - Google Patents
Verfahren zur Herstellung N-substituierter IndoleInfo
- Publication number
- DE2257710C3 DE2257710C3 DE19722257710 DE2257710A DE2257710C3 DE 2257710 C3 DE2257710 C3 DE 2257710C3 DE 19722257710 DE19722257710 DE 19722257710 DE 2257710 A DE2257710 A DE 2257710A DE 2257710 C3 DE2257710 C3 DE 2257710C3
- Authority
- DE
- Germany
- Prior art keywords
- indole
- methyl
- bromide
- substituted
- alkyl
- 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 17
- -1 N-substituted indoles Chemical class 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 16
- 150000002475 indoles Chemical class 0.000 claims description 10
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 13
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 10
- 229940100198 alkylating agent Drugs 0.000 description 10
- 239000002168 alkylating agent Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- AYMUQTNXKPEMLM-UHFFFAOYSA-N 1-bromononane Chemical compound CCCCCCCCCBr AYMUQTNXKPEMLM-UHFFFAOYSA-N 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- HGXYCDBNUQHARD-UHFFFAOYSA-N 1-decyl-2-methylindole Chemical compound C1=CC=C2N(CCCCCCCCCC)C(C)=CC2=C1 HGXYCDBNUQHARD-UHFFFAOYSA-N 0.000 description 1
- YPDNYTJCMSLJPZ-UHFFFAOYSA-N 1-dodecyl-2-methylindole Chemical compound C1=CC=C2N(CCCCCCCCCCCC)C(C)=CC2=C1 YPDNYTJCMSLJPZ-UHFFFAOYSA-N 0.000 description 1
- XMOWAIVXKJWQBJ-UHFFFAOYSA-N 1-ethyl-2-methylindole Chemical compound C1=CC=C2N(CC)C(C)=CC2=C1 XMOWAIVXKJWQBJ-UHFFFAOYSA-N 0.000 description 1
- UTWYKMGDHNCYTR-UHFFFAOYSA-N 1-heptyl-2-methylindole Chemical compound C1=CC=C2N(CCCCCCC)C(C)=CC2=C1 UTWYKMGDHNCYTR-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- BWNBLGQCCSCCHF-UHFFFAOYSA-N 2-ethyl-1h-indole Chemical compound C1=CC=C2NC(CC)=CC2=C1 BWNBLGQCCSCCHF-UHFFFAOYSA-N 0.000 description 1
- VGXYOARHYAJJDT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)indole Chemical compound C1=CC=C2N(CC(C)C)C(C)=CC2=C1 VGXYOARHYAJJDT-UHFFFAOYSA-N 0.000 description 1
- APQXTTYNLBMWEG-UHFFFAOYSA-N 2-methyl-1-nonylindole Chemical compound C1=CC=C2N(CCCCCCCCC)C(C)=CC2=C1 APQXTTYNLBMWEG-UHFFFAOYSA-N 0.000 description 1
- VZXPIBITTXSVHM-UHFFFAOYSA-N 2-methyl-1-octadecylindole Chemical compound C1=CC=C2N(CCCCCCCCCCCCCCCCCC)C(C)=CC2=C1 VZXPIBITTXSVHM-UHFFFAOYSA-N 0.000 description 1
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 1
- WUHIKCJBSKWNIC-UHFFFAOYSA-N 5-ethoxy-2-methyl-1h-indole Chemical compound CCOC1=CC=C2NC(C)=CC2=C1 WUHIKCJBSKWNIC-UHFFFAOYSA-N 0.000 description 1
- VSWGLJOQFUMFOQ-UHFFFAOYSA-N 5-methoxy-2-methyl-1h-indole Chemical compound COC1=CC=C2NC(C)=CC2=C1 VSWGLJOQFUMFOQ-UHFFFAOYSA-N 0.000 description 1
- DWAQDRSOVMLGRQ-UHFFFAOYSA-N 5-methoxyindole Chemical compound COC1=CC=C2NC=CC2=C1 DWAQDRSOVMLGRQ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1724071A CH556839A (de) | 1971-11-26 | 1971-11-26 | Verfahren zur herstellung n-substituierter indole in dimethylsulfoxyd. |
| CH1547472A CH572035A5 (en) | 1972-10-23 | 1972-10-23 | N-substd indole prodn - by treating with base in dmso or aprotic solvents and alkylating |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2257710A1 DE2257710A1 (de) | 1973-05-30 |
| DE2257710B2 DE2257710B2 (de) | 1981-05-27 |
| DE2257710C3 true DE2257710C3 (de) | 1982-04-15 |
Family
ID=25716494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722257710 Expired DE2257710C3 (de) | 1971-11-26 | 1972-11-24 | Verfahren zur Herstellung N-substituierter Indole |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS4992064A (OSRAM) |
| AU (1) | AU474547B2 (OSRAM) |
| BE (1) | BE791899A (OSRAM) |
| CA (1) | CA998680A (OSRAM) |
| CS (1) | CS161969B2 (OSRAM) |
| DE (1) | DE2257710C3 (OSRAM) |
| ES (1) | ES408977A1 (OSRAM) |
| FR (1) | FR2160884B1 (OSRAM) |
| GB (1) | GB1377901A (OSRAM) |
| IT (1) | IT973691B (OSRAM) |
| NL (1) | NL7215833A (OSRAM) |
| SU (1) | SU457216A3 (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW270114B (OSRAM) * | 1993-10-22 | 1996-02-11 | Hoffmann La Roche | |
| JP2009091294A (ja) * | 2007-10-09 | 2009-04-30 | Nippon Shokubai Co Ltd | Ｎ−（ヒドロキシアルキル）ピロール化合物の製造方法 |
-
0
- BE BE791899D patent/BE791899A/xx not_active IP Right Cessation
-
1972
- 1972-11-09 AU AU48692/72A patent/AU474547B2/en not_active Expired
- 1972-11-15 CA CA156,466A patent/CA998680A/en not_active Expired
- 1972-11-20 FR FR7241150A patent/FR2160884B1/fr not_active Expired
- 1972-11-22 GB GB5397972A patent/GB1377901A/en not_active Expired
- 1972-11-22 NL NL7215833A patent/NL7215833A/xx not_active Application Discontinuation
- 1972-11-23 CS CS797972A patent/CS161969B2/cs unknown
- 1972-11-23 IT IT5422372A patent/IT973691B/it active
- 1972-11-24 DE DE19722257710 patent/DE2257710C3/de not_active Expired
- 1972-11-24 SU SU1849384A patent/SU457216A3/ru active
- 1972-11-25 JP JP11772872A patent/JPS4992064A/ja active Pending
- 1972-11-25 ES ES408977A patent/ES408977A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT973691B (it) | 1974-06-10 |
| FR2160884A1 (OSRAM) | 1973-07-06 |
| AU4869272A (en) | 1974-05-09 |
| DE2257710A1 (de) | 1973-05-30 |
| JPS4992064A (OSRAM) | 1974-09-03 |
| CS161969B2 (OSRAM) | 1975-06-10 |
| NL7215833A (OSRAM) | 1973-05-29 |
| DE2257710B2 (de) | 1981-05-27 |
| CA998680A (en) | 1976-10-19 |
| SU457216A3 (ru) | 1975-01-15 |
| BE791899A (fr) | 1973-05-24 |
| FR2160884B1 (OSRAM) | 1975-04-25 |
| AU474547B2 (en) | 1976-07-29 |
| ES408977A1 (es) | 1976-03-16 |
| GB1377901A (en) | 1974-12-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: DERZEIT KEIN VERTRETER BESTELLT |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: SCHWABE, H., DIPL.-ING. SANDMAIR, K., DIPL.-CHEM. DR.JUR. DR.RER.NAT. MARX, L., DIPL.-PHYS. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |