DE2214488C3 - Verfahren zur Herstellung 1-substituierter 4-AminopyiTolin-3-one(2) - Google Patents
Verfahren zur Herstellung 1-substituierter 4-AminopyiTolin-3-one(2)Info
- Publication number
- DE2214488C3 DE2214488C3 DE19722214488 DE2214488A DE2214488C3 DE 2214488 C3 DE2214488 C3 DE 2214488C3 DE 19722214488 DE19722214488 DE 19722214488 DE 2214488 A DE2214488 A DE 2214488A DE 2214488 C3 DE2214488 C3 DE 2214488C3
- Authority
- DE
- Germany
- Prior art keywords
- mol
- yield
- benzene
- solution
- dried
- 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 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000010992 reflux Methods 0.000 description 6
- MZUSVMCRWTXEHF-UHFFFAOYSA-N 1-amino-2h-pyrrol-3-one Chemical class NN1CC(=O)C=C1 MZUSVMCRWTXEHF-UHFFFAOYSA-N 0.000 description 5
- HMXQIFUGFZEJEO-UHFFFAOYSA-N 1,2-dihydropyrrol-3-one Chemical class O=C1CNC=C1 HMXQIFUGFZEJEO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- VCPNLOMAQUZMBY-UHFFFAOYSA-N 4-chloro-3-oxobutanamide Chemical class NC(=O)CC(=O)CCl VCPNLOMAQUZMBY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- CJLSDBRIXZFCKV-UHFFFAOYSA-N 4-chloro-3-oxo-n-phenylbutanamide Chemical compound ClCC(=O)CC(=O)NC1=CC=CC=C1 CJLSDBRIXZFCKV-UHFFFAOYSA-N 0.000 description 1
- OMZUSMXJSPFYOY-UHFFFAOYSA-N 4-chloro-n-(2-chlorophenyl)-3-oxobutanamide Chemical compound ClCC(=O)CC(=O)NC1=CC=CC=C1Cl OMZUSMXJSPFYOY-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JBCSOBKDUKAJHR-UHFFFAOYSA-N ClO.NC1=CC=CC=C1 Chemical compound ClO.NC1=CC=CC=C1 JBCSOBKDUKAJHR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZXXJJIWWNMRXBX-UHFFFAOYSA-N NC(=O)CC(=O)CI Chemical class NC(=O)CC(=O)CI ZXXJJIWWNMRXBX-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH439271A CH543504A (de) | 1971-03-25 | 1971-03-25 | Verfahren zur Herstellung 1-substituierter 4-Aminopyrrolin-3-one-(2) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2214488A1 DE2214488A1 (de) | 1972-10-05 |
| DE2214488B2 DE2214488B2 (de) | 1980-03-13 |
| DE2214488C3 true DE2214488C3 (de) | 1980-11-06 |
Family
ID=4275258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722214488 Expired DE2214488C3 (de) | 1971-03-25 | 1972-03-24 | Verfahren zur Herstellung 1-substituierter 4-AminopyiTolin-3-one(2) |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT313891B (enExample) |
| BE (1) | BE781160A (enExample) |
| CA (1) | CA964661A (enExample) |
| CH (1) | CH543504A (enExample) |
| CS (1) | CS176186B2 (enExample) |
| DE (1) | DE2214488C3 (enExample) |
| FR (1) | FR2130704B1 (enExample) |
| GB (1) | GB1323020A (enExample) |
| IT (1) | IT988054B (enExample) |
| LU (1) | LU65031A1 (enExample) |
| NL (1) | NL7201106A (enExample) |
| SU (1) | SU470957A3 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH649282A5 (de) * | 1982-06-18 | 1985-05-15 | Lonza Ag | Verfahren zur herstellung von 4-(trialkylammonium)-acetoacetaryliden. |
| DE19944332A1 (de) * | 1999-09-16 | 2001-03-22 | Dresden Arzneimittel | Antikonvulsiv und anxiolytisch wirkende 4-Amino-1-aryl-1,5-dihydro-pyrrol-2-one und Verfahren zu deren Herstellung |
-
1971
- 1971-03-25 CH CH439271A patent/CH543504A/de not_active IP Right Cessation
- 1971-12-31 GB GB6096871A patent/GB1323020A/en not_active Expired
-
1972
- 1972-01-21 IT IT4784772A patent/IT988054B/it active
- 1972-01-27 NL NL7201106A patent/NL7201106A/xx not_active Application Discontinuation
- 1972-02-18 CS CS106072A patent/CS176186B2/cs unknown
- 1972-03-22 SU SU1763658A patent/SU470957A3/ru active
- 1972-03-23 LU LU65031D patent/LU65031A1/xx unknown
- 1972-03-23 BE BE781160A patent/BE781160A/xx unknown
- 1972-03-23 CA CA137,930A patent/CA964661A/en not_active Expired
- 1972-03-24 FR FR7210521A patent/FR2130704B1/fr not_active Expired
- 1972-03-24 AT AT258572A patent/AT313891B/de not_active IP Right Cessation
- 1972-03-24 DE DE19722214488 patent/DE2214488C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2130704A1 (enExample) | 1972-11-03 |
| LU65031A1 (enExample) | 1972-12-07 |
| IT988054B (it) | 1975-04-10 |
| GB1323020A (en) | 1973-07-11 |
| DE2214488B2 (de) | 1980-03-13 |
| FR2130704B1 (enExample) | 1977-04-01 |
| BE781160A (fr) | 1972-09-25 |
| NL7201106A (enExample) | 1972-09-27 |
| CA964661A (en) | 1975-03-18 |
| CS176186B2 (enExample) | 1977-06-30 |
| AT313891B (de) | 1974-03-11 |
| DE2214488A1 (de) | 1972-10-05 |
| SU470957A3 (ru) | 1975-05-15 |
| CH543504A (de) | 1973-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |