Triethylamine → 2-Pyrrolidinone, 1-(8-quinolinyl)-

HRID 1902825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1902825
Cl[CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[NH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2.C(N(CC)CC)C>C(COC)OC>[N:17]1[C:18]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])[CH:14]=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 113598-AminoquinolineHCID 783704-Chlorobutyryl chloride

Produkt 1

HCID 30614652-Pyrrolidinone, 1-(8-quinolinyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

4-Chlorobutryl chloride (388.0 g) was added at 40° to a solution of technical grade 8-aminoquinoline (3396.5 g) and triethylamine (278.3 g) in dimethoxyethane (2 l). After stirring overnight at ambient temperature the solids were filtered off. The filtrate was concentrated prior to additon of 13% potassium tert-butoxide in tert-butanol (2486 g) at 25°-30°. After two hours the mixture was neutralized with dilute hydrochloric acid. The slurry obtained by partial removal of the solvent was extracted three times with methylene chloride. The combined extracts were washed with water, dried over magnesium sulphate, filtered and concentrated. Ether (1 l) was added while cooling to 0°. Filtration, followed by vacuum-drying afforded 1-(8-quinolyl)-2-pyrrolidinone.

Aufarbeitung

  1. filtrationwere filtered off
  2. concentrationThe filtrate was concentrated
  3. customat 25°-30°
  4. waitAfter two hours the mixture was neutralized with dilute hydrochloric acid
  5. customThe slurry obtained by partial removal of the solvent
  6. extractionwas extracted three times with methylene chloride
  7. washThe combined extracts were washed with water
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. additionEther (1 l) was added
  12. temperaturewhile cooling to 0°
  13. filtrationFiltration
  14. customby vacuum-drying

Quellen und Nachweise

ORD-Eintrag
ord-2a7bc443250f49458357111b52ca8f3b
Quelldatensatz
uspto-grants-1982_12
Patentnummer
US04366158

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