BE514020A - - Google Patents
Info
- Publication number
- BE514020A BE514020A BE514020DA BE514020A BE 514020 A BE514020 A BE 514020A BE 514020D A BE514020D A BE 514020DA BE 514020 A BE514020 A BE 514020A
- Authority
- BE
- Belgium
- Prior art keywords
- nitro
- amino
- lower alkoxy
- mixture
- acid
- Prior art date
Links
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- PCWRBWMEDZMOIA-UHFFFAOYSA-N [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCC Chemical compound [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCC PCWRBWMEDZMOIA-UHFFFAOYSA-N 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 7
- -1 1-amino-2-isobutoxybenzamide Chemical compound 0.000 claims description 5
- 239000003638 reducing agent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- XBQYOLIOBABGEO-UHFFFAOYSA-N 4-amino-2-(2-methylpropoxy)benzamide Chemical compound CC(C)COC1=CC(N)=CC=C1C(N)=O XBQYOLIOBABGEO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 13
- 230000000875 corresponding Effects 0.000 description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 235000010233 benzoic acid Nutrition 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- JBJIBKWPYLFRRD-UHFFFAOYSA-N 4-amino-2-ethoxybenzamide Chemical compound CCOC1=CC(N)=CC=C1C(N)=O JBJIBKWPYLFRRD-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012256 powdered iron Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229940054066 Benzamide antipsychotics Drugs 0.000 description 4
- 150000003936 benzamides Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 150000001559 benzoic acids Chemical class 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- DZNPHVPBCNZVGW-UHFFFAOYSA-N 2-hydroxy-4-nitrobenzonitrile Chemical compound OC1=CC([N+]([O-])=O)=CC=C1C#N DZNPHVPBCNZVGW-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000008359 benzonitriles Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- BSIOETYGDXDWBR-UHFFFAOYSA-N 2-ethoxy-4-nitrobenzoic acid Chemical compound CCOC1=CC([N+]([O-])=O)=CC=C1C(O)=O BSIOETYGDXDWBR-UHFFFAOYSA-N 0.000 description 2
- RWXNPKHTHFLAAN-UHFFFAOYSA-N 2-ethoxy-4-nitrobenzonitrile Chemical compound CCOC1=CC([N+]([O-])=O)=CC=C1C#N RWXNPKHTHFLAAN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- CWPAFDWNYPPNPW-UHFFFAOYSA-N [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCC(C)C Chemical compound [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCC(C)C CWPAFDWNYPPNPW-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- IMAGJJUELPRODU-UHFFFAOYSA-N 2-butoxybenzonitrile Chemical compound CCCCOC1=CC=CC=C1C#N IMAGJJUELPRODU-UHFFFAOYSA-N 0.000 description 1
- UHSPFGXDTWIDHO-UHFFFAOYSA-N 4-amino-2-(3-methylbutoxy)benzamide Chemical compound CC(C)CCOC1=CC(N)=CC=C1C(N)=O UHSPFGXDTWIDHO-UHFFFAOYSA-N 0.000 description 1
- OIYHHPPBQSGIJM-UHFFFAOYSA-N 4-amino-2-hexoxybenzamide Chemical compound CCCCCCOC1=CC(N)=CC=C1C(N)=O OIYHHPPBQSGIJM-UHFFFAOYSA-N 0.000 description 1
- XQZJGIKHMOMFBR-UHFFFAOYSA-N 4-amino-2-propoxybenzamide Chemical compound CCCOC1=CC(N)=CC=C1C(N)=O XQZJGIKHMOMFBR-UHFFFAOYSA-N 0.000 description 1
- FOBSRWRUBVWBMC-UHFFFAOYSA-N 4-nitro-2-propoxybenzonitrile Chemical compound CCCOC1=CC([N+]([O-])=O)=CC=C1C#N FOBSRWRUBVWBMC-UHFFFAOYSA-N 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L Iron(II) sulfate Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- PHUYPECMCDDONQ-UHFFFAOYSA-N [N+](=O)([O-])C1=CC(=C(C#N)C=C1)OCCCC Chemical compound [N+](=O)([O-])C1=CC(=C(C#N)C=C1)OCCCC PHUYPECMCDDONQ-UHFFFAOYSA-N 0.000 description 1
- DUWJCZCGOQPAKN-UHFFFAOYSA-N [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCCC(C)C Chemical compound [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCCC(C)C DUWJCZCGOQPAKN-UHFFFAOYSA-N 0.000 description 1
- FGGIBGUMJMPHAV-UHFFFAOYSA-N [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCCCC Chemical compound [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCCCC FGGIBGUMJMPHAV-UHFFFAOYSA-N 0.000 description 1
- KBLJHYPPXFWKMX-UHFFFAOYSA-N [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCCCC(C)C Chemical compound [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCCCC(C)C KBLJHYPPXFWKMX-UHFFFAOYSA-N 0.000 description 1
- UYXXGWKJDGMREG-UHFFFAOYSA-N [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCCCCCC Chemical compound [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCCCCCC UYXXGWKJDGMREG-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000202 analgesic Effects 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003111 delayed Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VMIPKNWALSUQDX-UHFFFAOYSA-N ethyl 2-ethoxy-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C=C1OCC VMIPKNWALSUQDX-UHFFFAOYSA-N 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002140 halogenating Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE514020A true BE514020A (el) |
Family
ID=151960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE514020D BE514020A (el) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE514020A (el) |
-
0
- BE BE514020D patent/BE514020A/fr unknown
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