DE2050496A1 - Verfahren zur Herstellung von 7 Alkyl und 7 Cycloalkjlalkyl 4 (4 pyridyl) 2,2 dialkyl 2H chromen 5 öl Verbindungen - Google Patents
Verfahren zur Herstellung von 7 Alkyl und 7 Cycloalkjlalkyl 4 (4 pyridyl) 2,2 dialkyl 2H chromen 5 öl VerbindungenInfo
- Publication number
- DE2050496A1 DE2050496A1 DE19702050496 DE2050496A DE2050496A1 DE 2050496 A1 DE2050496 A1 DE 2050496A1 DE 19702050496 DE19702050496 DE 19702050496 DE 2050496 A DE2050496 A DE 2050496A DE 2050496 A1 DE2050496 A1 DE 2050496A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- alkyl
- pyridyl
- iii
- reaction
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 20
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 title claims description 7
- 125000000217 alkyl group Chemical group 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 title description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 28
- -1 3-methyl-2-octyl Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 229960000956 coumarin Drugs 0.000 claims description 6
- 235000001671 coumarin Nutrition 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- UNVNVCMGCFNMQD-UHFFFAOYSA-N 2h-chromen-5-ol Chemical class O1CC=CC2=C1C=CC=C2O UNVNVCMGCFNMQD-UHFFFAOYSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ZTTJDMREUVSBOB-UHFFFAOYSA-N C(CCCCCC)C1=CC(=C2C(=CC(OC2=C1)=O)C1=CC=NC=C1)O Chemical compound C(CCCCCC)C1=CC(=C2C(=CC(OC2=C1)=O)C1=CC=NC=C1)O ZTTJDMREUVSBOB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB50703/69A GB1280044A (en) | 1969-10-15 | 1969-10-15 | Preparation of pyridyl chromenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2050496A1 true DE2050496A1 (de) | 1971-04-22 |
Family
ID=10457014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702050496 Pending DE2050496A1 (de) | 1969-10-15 | 1970-10-14 | Verfahren zur Herstellung von 7 Alkyl und 7 Cycloalkjlalkyl 4 (4 pyridyl) 2,2 dialkyl 2H chromen 5 öl Verbindungen |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT298487B (enrdf_load_stackoverflow) |
| BE (1) | BE757454R (enrdf_load_stackoverflow) |
| DE (1) | DE2050496A1 (enrdf_load_stackoverflow) |
| ES (1) | ES384217A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2070131B2 (enrdf_load_stackoverflow) |
| GB (1) | GB1280044A (enrdf_load_stackoverflow) |
| IE (1) | IE34540B1 (enrdf_load_stackoverflow) |
| NL (1) | NL7014946A (enrdf_load_stackoverflow) |
| ZA (1) | ZA706821B (enrdf_load_stackoverflow) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE713490A (enrdf_load_stackoverflow) * | 1967-04-14 | 1968-10-10 |
-
0
- BE BE757454D patent/BE757454R/xx active
-
1969
- 1969-10-15 GB GB50703/69A patent/GB1280044A/en not_active Expired
-
1970
- 1970-09-21 IE IE1218/70A patent/IE34540B1/xx unknown
- 1970-10-02 ES ES384217A patent/ES384217A1/es not_active Expired
- 1970-10-07 ZA ZA706821A patent/ZA706821B/xx unknown
- 1970-10-12 NL NL7014946A patent/NL7014946A/xx unknown
- 1970-10-13 FR FR7036865A patent/FR2070131B2/fr not_active Expired
- 1970-10-14 AT AT926270A patent/AT298487B/de not_active IP Right Cessation
- 1970-10-14 DE DE19702050496 patent/DE2050496A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE757454R (fr) | 1971-04-13 |
| GB1280044A (en) | 1972-07-05 |
| FR2070131B2 (enrdf_load_stackoverflow) | 1974-09-20 |
| NL7014946A (enrdf_load_stackoverflow) | 1971-04-19 |
| IE34540B1 (en) | 1975-06-11 |
| ES384217A1 (es) | 1973-01-16 |
| IE34540L (en) | 1971-04-15 |
| AT298487B (de) | 1972-05-10 |
| ZA706821B (en) | 1971-12-29 |
| FR2070131A2 (enrdf_load_stackoverflow) | 1971-09-10 |
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