BE549603A - - Google Patents
Info
- Publication number
- BE549603A BE549603A BE549603DA BE549603A BE 549603 A BE549603 A BE 549603A BE 549603D A BE549603D A BE 549603DA BE 549603 A BE549603 A BE 549603A
- Authority
- BE
- Belgium
- Prior art keywords
- amino
- salts
- benzyl
- indol
- residue
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000011780 sodium chloride Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- LMDPYYUISNUGGT-UHFFFAOYSA-N 2-(2-aminophenyl)acetonitrile Chemical compound NC1=CC=CC=C1CC#N LMDPYYUISNUGGT-UHFFFAOYSA-N 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 6
- -1 carbethoxy-methyl residue Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical group C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 3
- 230000001034 aminogenic Effects 0.000 claims description 3
- 150000007962 benzene acetonitriles Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 3
- SZFPOMLSQTZGNM-UHFFFAOYSA-N 1-methylindol-2-amine Chemical compound C1=CC=C2N(C)C(N)=CC2=C1 SZFPOMLSQTZGNM-UHFFFAOYSA-N 0.000 claims description 2
- YMOPFJHCVLXQEO-UHFFFAOYSA-N C(=O)(OCC)CN1C(=CC2=CC=CC=C12)N Chemical compound C(=O)(OCC)CN1C(=CC2=CC=CC=C12)N YMOPFJHCVLXQEO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- KRKOUYGRFMARHC-UHFFFAOYSA-N 1-benzylindol-2-amine Chemical compound NC1=CC2=CC=CC=C2N1CC1=CC=CC=C1 KRKOUYGRFMARHC-UHFFFAOYSA-N 0.000 claims 1
- BABQUGZTENNQSB-UHFFFAOYSA-N 5-methoxy-1-methylindol-2-amine Chemical compound COC1=CC=C2N(C)C(N)=CC2=C1 BABQUGZTENNQSB-UHFFFAOYSA-N 0.000 claims 1
- LSZQSKSNLUSAHW-UHFFFAOYSA-N NC=1N(C2=CC=CC=C2C1)CC Chemical compound NC=1N(C2=CC=CC=C2C1)CC LSZQSKSNLUSAHW-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 230000000875 corresponding Effects 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ZFDZPKNZFAHZCY-UHFFFAOYSA-N 2-(2-amino-5-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(N)C(CC#N)=C1 ZFDZPKNZFAHZCY-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 230000001603 reducing Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N Benzyl cyanide Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- PZZCRWCCMIBFPB-UHFFFAOYSA-N CN1C(=CC2=CC(=CC=C12)OCC1=CC=CC=C1)N Chemical compound CN1C(=CC2=CC(=CC=C12)OCC1=CC=CC=C1)N PZZCRWCCMIBFPB-UHFFFAOYSA-N 0.000 description 1
- ZICDCAIWMCAPLM-UHFFFAOYSA-N Cl.C(C1=CC=CC=C1)N1C(=CC2=CC=CC=C12)N Chemical compound Cl.C(C1=CC=CC=C1)N1C(=CC2=CC=CC=C12)N ZICDCAIWMCAPLM-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N Ethyl iodide Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M Silver chloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01S—RADIO DIRECTION-FINDING; RADIO NAVIGATION; DETERMINING DISTANCE OR VELOCITY BY USE OF RADIO WAVES; LOCATING OR PRESENCE-DETECTING BY USE OF THE REFLECTION OR RERADIATION OF RADIO WAVES; ANALOGOUS ARRANGEMENTS USING OTHER WAVES
- G01S15/00—Systems using the reflection or reradiation of acoustic waves, e.g. sonar systems
- G01S15/88—Sonar systems specially adapted for specific applications
- G01S15/96—Sonar systems specially adapted for specific applications for locating fish
-
- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
Landscapes
- Engineering & Computer Science (AREA)
- Radar, Positioning & Navigation (AREA)
- Remote Sensing (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Acoustics & Sound (AREA)
- Computer Networks & Wireless Communication (AREA)
- General Physics & Mathematics (AREA)
- Indole Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE549603A true BE549603A (zh) |
Family
ID=175780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE549603D BE549603A (zh) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE549603A (zh) |
-
0
- BE BE549603D patent/BE549603A/fr unknown
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