JPH0480904B2 - - Google Patents
Info
- Publication number
- JPH0480904B2 JPH0480904B2 JP58062055A JP6205583A JPH0480904B2 JP H0480904 B2 JPH0480904 B2 JP H0480904B2 JP 58062055 A JP58062055 A JP 58062055A JP 6205583 A JP6205583 A JP 6205583A JP H0480904 B2 JPH0480904 B2 JP H0480904B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- alkylpyridine
- alkylated
- temperature
- carbon atoms
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 claims description 70
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 44
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 33
- 229910052708 sodium Inorganic materials 0.000 claims description 32
- 239000011734 sodium Substances 0.000 claims description 32
- 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 claims description 31
- 239000000047 product Substances 0.000 claims description 28
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 25
- 239000006185 dispersion Substances 0.000 claims description 24
- 238000010992 reflux Methods 0.000 claims description 20
- 159000000000 sodium salts Chemical class 0.000 claims description 19
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000003973 alkyl amines Chemical class 0.000 claims description 17
- 238000006900 dealkylation reaction Methods 0.000 claims description 17
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical group CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 16
- 230000020335 dealkylation Effects 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 12
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical group CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 10
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical group CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- AFJDGRCBXVYTAW-UHFFFAOYSA-N butanamide;sodium Chemical compound [Na].CCCC(N)=O AFJDGRCBXVYTAW-UHFFFAOYSA-N 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000011260 aqueous acid Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 239000012298 atmosphere Substances 0.000 claims 1
- 229940071870 hydroiodic acid Drugs 0.000 claims 1
- 238000012423 maintenance Methods 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 description 23
- 238000005576 amination reaction Methods 0.000 description 15
- AXIQBCPOTNAYQH-UHFFFAOYSA-N n-butyl-5-methylpyridin-2-amine Chemical compound CCCCNC1=CC=C(C)C=N1 AXIQBCPOTNAYQH-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 8
- 239000012071 phase Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 6
- -1 amide compound Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- DCJSWFCTYSFVAY-UHFFFAOYSA-N n-butyl-3-methylpyridin-2-amine Chemical compound CCCCNC1=NC=CC=C1C DCJSWFCTYSFVAY-UHFFFAOYSA-N 0.000 description 4
- KFHLRMWLLJSLHV-UHFFFAOYSA-N n-butyl-5-methylpyridin-2-amine;hydrobromide Chemical compound Br.CCCCNC1=CC=C(C)C=N1 KFHLRMWLLJSLHV-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- ZBNJVQZTBKMTRK-UHFFFAOYSA-N n-butylpyridin-2-amine Chemical compound CCCCNC1=CC=CC=N1 ZBNJVQZTBKMTRK-UHFFFAOYSA-N 0.000 description 2
- UUMQKWWKCDCMJS-UHFFFAOYSA-N n-cyclohexylpyridin-2-amine Chemical compound C1CCCCC1NC1=CC=CC=N1 UUMQKWWKCDCMJS-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- IHTBKVYBYWJXII-UHFFFAOYSA-N 3-butylquinolin-2-amine Chemical compound C1=CC=C2N=C(N)C(CCCC)=CC2=C1 IHTBKVYBYWJXII-UHFFFAOYSA-N 0.000 description 1
- DMGGLIWGZFZLIY-UHFFFAOYSA-N 3-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=C[N+]([O-])=C1 DMGGLIWGZFZLIY-UHFFFAOYSA-N 0.000 description 1
- AQIIVEISJBBUCR-UHFFFAOYSA-N 4-(3-phenylpropyl)pyridine Chemical group C=1C=NC=CC=1CCCC1=CC=CC=C1 AQIIVEISJBBUCR-UHFFFAOYSA-N 0.000 description 1
- JAWZAONCXMJLFT-UHFFFAOYSA-N 4-propylpyridine Chemical compound CCCC1=CC=NC=C1 JAWZAONCXMJLFT-UHFFFAOYSA-N 0.000 description 1
- IAPOAEZRYHLSAT-UHFFFAOYSA-N 5-methyl-n-phenylpyridin-2-amine Chemical compound N1=CC(C)=CC=C1NC1=CC=CC=C1 IAPOAEZRYHLSAT-UHFFFAOYSA-N 0.000 description 1
- NAYHTVLKACWGFO-UHFFFAOYSA-N 5-methylpyridin-2-amine;hydrobromide Chemical compound Br.CC1=CC=C(N)N=C1 NAYHTVLKACWGFO-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 241000219322 Dianthus Species 0.000 description 1
- 206010016173 Fall Diseases 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical class C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- XVEWGKNQWNGFPE-UHFFFAOYSA-N n',n'-dimethyl-n-(6-methylpyridin-2-yl)ethane-1,2-diamine Chemical compound CN(C)CCNC1=CC=CC(C)=N1 XVEWGKNQWNGFPE-UHFFFAOYSA-N 0.000 description 1
- PBPMFHCGVZTYHV-UHFFFAOYSA-N n',n'-dimethyl-n-pyridin-2-ylethane-1,2-diamine Chemical compound CN(C)CCNC1=CC=CC=N1 PBPMFHCGVZTYHV-UHFFFAOYSA-N 0.000 description 1
- FSCKKQPHNYTTGE-UHFFFAOYSA-N n',n'-dimethyl-n-quinolin-2-ylethane-1,2-diamine Chemical compound C1=CC=CC2=NC(NCCN(C)C)=CC=C21 FSCKKQPHNYTTGE-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- TYUZGTNWNYXSHE-UHFFFAOYSA-N n-(5-methylpyridin-2-yl)-n-phenylbenzamide Chemical compound N1=CC(C)=CC=C1N(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 TYUZGTNWNYXSHE-UHFFFAOYSA-N 0.000 description 1
- WYHXNQXDQQMTQI-UHFFFAOYSA-N n-benzylpyridin-2-amine Chemical compound C=1C=CC=CC=1CNC1=CC=CC=N1 WYHXNQXDQQMTQI-UHFFFAOYSA-N 0.000 description 1
- OECWVHLMORFOCL-UHFFFAOYSA-N n-butylquinolin-2-amine Chemical compound C1=CC=CC2=NC(NCCCC)=CC=C21 OECWVHLMORFOCL-UHFFFAOYSA-N 0.000 description 1
- DKNYQWSMAYKEEW-UHFFFAOYSA-N n-cyclohexylquinolin-2-amine Chemical compound C1CCCCC1NC1=CC=C(C=CC=C2)C2=N1 DKNYQWSMAYKEEW-UHFFFAOYSA-N 0.000 description 1
- XCIVYFPIDWCXHK-UHFFFAOYSA-N n-dodecylpyridin-2-amine Chemical compound CCCCCCCCCCCCNC1=CC=CC=N1 XCIVYFPIDWCXHK-UHFFFAOYSA-N 0.000 description 1
- IVCDYLIODNNGLA-UHFFFAOYSA-N n-heptylpyridin-2-amine Chemical compound CCCCCCCNC1=CC=CC=N1 IVCDYLIODNNGLA-UHFFFAOYSA-N 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- POVSMFKXVSNGSU-UHFFFAOYSA-N n-methylquinolin-2-amine Chemical compound C1=CC=CC2=NC(NC)=CC=C21 POVSMFKXVSNGSU-UHFFFAOYSA-N 0.000 description 1
- WFOFSUPMQDLYOM-UHFFFAOYSA-N n-phenylbenzenecarboximidoyl chloride Chemical compound C=1C=CC=CC=1C(Cl)=NC1=CC=CC=C1 WFOFSUPMQDLYOM-UHFFFAOYSA-N 0.000 description 1
- HUDSSSKDWYXKGP-UHFFFAOYSA-N n-phenylpyridin-2-amine Chemical compound C=1C=CC=NC=1NC1=CC=CC=C1 HUDSSSKDWYXKGP-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US366599 | 1982-04-08 | ||
| US06/366,599 US4405790A (en) | 1982-04-08 | 1982-04-08 | Process for preparing 2-alkylamino- and 2-amino-5-alkylpyridines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58192870A JPS58192870A (ja) | 1983-11-10 |
| JPH0480904B2 true JPH0480904B2 (ja) | 1992-12-21 |
Family
ID=23443682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58062055A Granted JPS58192870A (ja) | 1982-04-08 | 1983-04-08 | ïŒâã¢ã«ãã«ã¢ããâããã³ïŒâã¢ããâïŒâã¢ã«ãã«ããªãžã³ã®è£œé æ¹æ³ |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4405790A (ja) |
| EP (1) | EP0091790B1 (ja) |
| JP (1) | JPS58192870A (ja) |
| CA (1) | CA1219589A (ja) |
| DE (1) | DE3380846D1 (ja) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0112707B1 (en) * | 1982-12-23 | 1987-11-04 | Smith Kline & French Laboratories Limited | Aminopyrimidinone derivatives as histamine h1-antagonists |
| DE4232175A1 (de) * | 1992-04-15 | 1993-10-21 | Bayer Ag | Verfahren zur Herstellung von 2-Amino-5-methyl-pyridin |
| IL114314A (en) * | 1994-06-24 | 2000-12-06 | Reilly Ind Inc | Amination of pyridine bases |
| US5808081A (en) * | 1995-06-26 | 1998-09-15 | Reilly Industries, Inc. | Chichibabin aminations of pyridine bases |
| ATE295365T1 (de) * | 2000-02-09 | 2005-05-15 | Novartis Pharma Gmbh | Pyridinderivative als angiogenese- und/oder vegf- rezeptor-tyrosinkinase-inhibitoren |
| CN106496105B (zh) * | 2016-08-31 | 2019-01-11 | å京红倪é³çç©ååŠæéèŽ£ä»»å ¬åž | äžç§3-ç²åºå¡å¶æ°šåå¶å€2-æ°šåº-5-ç²åºå¡å¶çæ¹æ³ |
| CN111778720A (zh) * | 2020-07-10 | 2020-10-16 | æž©å·å執æ饰æéå ¬åž | äžç§é²æœ®ç®è¡£åå ¶å å·¥å·¥èº |
-
1982
- 1982-04-08 US US06/366,599 patent/US4405790A/en not_active Expired - Lifetime
-
1983
- 1983-04-07 DE DE8383301959T patent/DE3380846D1/de not_active Expired
- 1983-04-07 EP EP83301959A patent/EP0091790B1/en not_active Expired
- 1983-04-07 CA CA000425411A patent/CA1219589A/en not_active Expired
- 1983-04-08 JP JP58062055A patent/JPS58192870A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1219589A (en) | 1987-03-24 |
| DE3380846D1 (en) | 1989-12-21 |
| US4405790A (en) | 1983-09-20 |
| JPS58192870A (ja) | 1983-11-10 |
| EP0091790A3 (en) | 1984-11-14 |
| EP0091790A2 (en) | 1983-10-19 |
| EP0091790B1 (en) | 1989-11-15 |
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