PL52809B1 - - Google Patents
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- Publication number
- PL52809B1 PL52809B1 PL104984A PL10498464A PL52809B1 PL 52809 B1 PL52809 B1 PL 52809B1 PL 104984 A PL104984 A PL 104984A PL 10498464 A PL10498464 A PL 10498464A PL 52809 B1 PL52809 B1 PL 52809B1
- Authority
- PL
- Poland
- Prior art keywords
- acetic acid
- tetrahydroquinolyl
- benzylamine
- ester
- condensed
- Prior art date
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- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
- -1 carboxybenzyl Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- IBNYPYJMTVXJSZ-UHFFFAOYSA-N 2-(3,4-dihydro-2h-quinolin-1-yl)acetic acid Chemical compound C1=CC=C2N(CC(=O)O)CCCC2=C1 IBNYPYJMTVXJSZ-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- CFVILHFXMRQYSG-UHFFFAOYSA-N 2-quinolin-6-ylacetic acid Chemical compound N1=CC=CC2=CC(CC(=O)O)=CC=C21 CFVILHFXMRQYSG-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000012320 chlorinating reagent Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- UZJLYRRDVFWSGA-UHFFFAOYSA-N n-benzylacetamide Chemical compound CC(=O)NCC1=CC=CC=C1 UZJLYRRDVFWSGA-UHFFFAOYSA-N 0.000 description 1
Description
9,27 g (0,03 mola) estru etylowego kwasu N-ben- zylo-6-(l,2,3,4-tetrahydrochinolilo)-octowego ogrze¬ wano z 3,75 g (0,035 mola) benzyloaminy. Otrzy¬ mano z wydajnoscia okolo 85% benzyloamid kwa¬ su N-benzylo-0-(l,2,3,4-tetrahyclrochinolilo)-octowe¬ go, który oczyszczano przez krystalizacje z etano¬ lu, temperatura topnienia 99—9«9,50C. PL
Claims (2)
- Zastrzezenia patentowe 1. Sposób wytwarzania benzyloamidów kwasów 6-(l,2,3,4-tetrahydrochinolilo)-octowych o wzo¬ rze 1, w którym R oznacza atom wodoru lub reszte zawierajaca pierscien aromatyczny lub heterocykliczny azotowy np. benzylowa, kar- boksybenzylowa, pirydylometylowa, 2-(N-mety- lo-2-piperydylo)-etyIowa, znamienny tym, ze kwas 6-chinolilooctowy lub jego ester uwo- darnia sie wodorem pod cisnieniem zwlaszcza w obecnosci katalizatora palladowego, po czym w przypadku uwodarniania kwasu otrzymany kwas 6-(l,2,3,4-tetrahydrochinolilooctowy prze¬ prowadza sie w znany sposób w ester, a na¬ stepnie ester kwasu 6-(l,2,3,4-tetrahydrochino- liloj-octowego w celu otrzymania produktu, w którym R oznacza atom wodoru, kondensu- je sie bezposrednio z benzyloamina, a w celu otrzymania produktu, w którym R oznacza wyzej wymieniona reszte zawierajaca pierscien aromatyczny lub heterocykliczny azotowy pod¬ daje sie dzialaniu zwiazku stanowiacego pola¬ czenie tej reszty z chlorem, a nastepnie otrzy¬ many produkt kondensuje sie z benzyloamina.
- 2. Odmiana sposobu wedlug zastrz. 1, znamienna tym, ze na kwas 6-(l,2,3,4-tetrahydrochinolilo)- -octowy dziala sie srodkiem chlorujacym zwlaszcza chlorkiem tionylu, a otrzymany chlorek kwasowy kondensuje sie z benzylo¬ amina.KI. 12 p,1/10 52809 MKP C 07 d f^^rCWOM CH2 f~\ I i? kzóri yitr^r CHtCONHCHt/ Nzór2 PL
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL52809B1 true PL52809B1 (pl) | 1967-02-25 |
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