IL25878A - Process for the preparation of indane derivatives - Google Patents
Process for the preparation of indane derivativesInfo
- Publication number
- IL25878A IL25878A IL25878A IL2587866A IL25878A IL 25878 A IL25878 A IL 25878A IL 25878 A IL25878 A IL 25878A IL 2587866 A IL2587866 A IL 2587866A IL 25878 A IL25878 A IL 25878A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- group
- aqueous
- acidic compound
- lower alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title description 4
- 125000003392 indanyl group Chemical class C1(CCC2=CC=CC=C12)* 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- -1 trimethylamine trimethylamine triethylamine piperidine piperidine phosphate Chemical compound 0.000 claims description 3
- HNIASRFAODUYDL-UHFFFAOYSA-N acetyl acetate;sodium Chemical compound [Na].CC(=O)OC(C)=O HNIASRFAODUYDL-UHFFFAOYSA-N 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ISDUIDRCFYENQN-UHFFFAOYSA-N 5-oxohept-6-enoic acid Chemical compound OC(=O)CCCC(=O)C=C ISDUIDRCFYENQN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000551547 Dione <red algae> Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 101150007166 ensa gene Proteins 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000002468 indanes Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ONGNQDROOOWKJT-UHFFFAOYSA-N methyl 5-oxohept-6-enoate Chemical compound COC(=O)CCCC(=O)C=C ONGNQDROOOWKJT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940032007 methylethyl ketone Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- JVZXXHPGADCTTB-UHFFFAOYSA-M sodium;acetyl acetate;acetate Chemical compound [Na+].CC([O-])=O.CC(=O)OC(C)=O JVZXXHPGADCTTB-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/80—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings
- C07C59/82—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings the keto group being part of a ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR20062A FR1446408A (fr) | 1965-06-09 | 1965-06-09 | Nouveau procédé de préparation de certains dérivés de l'indane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL25878A true IL25878A (en) | 1969-11-12 |
Family
ID=8581313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL25878A IL25878A (en) | 1965-06-09 | 1966-05-31 | Process for the preparation of indane derivatives |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3527791A (en, 2012) |
| AT (1) | AT270891B (en, 2012) |
| BE (1) | BE681893A (en, 2012) |
| CH (1) | CH462153A (en, 2012) |
| DE (1) | DE1593310B1 (en, 2012) |
| DK (1) | DK132020C (en, 2012) |
| ES (1) | ES327674A1 (en, 2012) |
| FR (1) | FR1446408A (en, 2012) |
| GB (1) | GB1096766A (en, 2012) |
| IL (1) | IL25878A (en, 2012) |
| NL (1) | NL129203C (en, 2012) |
| SE (1) | SE320658B (en, 2012) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1364556A (fr) * | 1962-03-06 | 1964-06-26 | Roussel Uclaf | Nouveau procédé de synthèse de stéroïdes et de composés apparentés et produits utilisés dans ce procédé |
| NL124123C (en, 2012) * | 1963-04-26 | |||
| NL130309C (en, 2012) * | 1963-11-29 |
-
1965
- 1965-06-09 FR FR20062A patent/FR1446408A/fr not_active Expired
-
1966
- 1966-05-31 BE BE681893D patent/BE681893A/xx unknown
- 1966-05-31 IL IL25878A patent/IL25878A/en unknown
- 1966-06-01 US US554356A patent/US3527791A/en not_active Expired - Lifetime
- 1966-06-07 GB GB25335/66A patent/GB1096766A/en not_active Expired
- 1966-06-07 AT AT541966A patent/AT270891B/de active
- 1966-06-07 DK DK291566A patent/DK132020C/da active
- 1966-06-08 DE DE19661593310 patent/DE1593310B1/de not_active Withdrawn
- 1966-06-08 NL NL6607920A patent/NL129203C/xx active
- 1966-06-08 SE SE7875/66A patent/SE320658B/xx unknown
- 1966-06-08 ES ES0327674A patent/ES327674A1/es not_active Expired
- 1966-06-08 CH CH825666A patent/CH462153A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH462153A (fr) | 1968-09-15 |
| SE320658B (en, 2012) | 1970-02-16 |
| ES327674A1 (es) | 1967-03-16 |
| DK132020B (da) | 1975-10-13 |
| DE1593310B1 (de) | 1971-07-01 |
| DK132020C (da) | 1976-03-08 |
| US3527791A (en) | 1970-09-08 |
| BE681893A (en, 2012) | 1966-11-30 |
| NL129203C (en, 2012) | 1970-07-15 |
| FR1446408A (fr) | 1966-07-22 |
| AT270891B (de) | 1969-05-12 |
| GB1096766A (en) | 1967-12-29 |
| NL6607920A (en, 2012) | 1966-12-12 |
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