7-Chloro-2-(5-acetoxybenzofuran-2-yl)quinoline → 7-Chloro-2-(5-hydroxybenzofuran-2-yl)quinoline

HRID 2258507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2258507
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([O:21]C(=O)C)=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1>CO.[OH-].[Na+].CN(C)C=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 1

HCID 229221197-Chloro-2-(5-acetoxybenzofuran-2-yl)quinoline

Produkt 1

HCID 229222067-Chloro-2-(5-hydroxybenzofuran-2-yl)quinolineAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a suspension of 7-chloro-2-(5-acetoxybenzofuran-2-yl)quinoline (16.7 g) in methanol (400 ml), 1N aqueous sodium hydroxide (50 ml) was added at ambient temperature. The mixture was stirred for 1 day. After the solvent was removed under reduced pressure, the residue was suspended with water, and adjusted to pH 6-7 with diluted aqueous hydrochloric acid. After the resulting suspension was stirred at ambient temperature for 1 hour, the precipitates were collected by filtration, washed with water and dried in vacuo to give crude material (15 g). The crude material was dissolved in N,N-dimethylformamide (200 ml) at 80° C., and the resulting solution was allowed to stand at ambient temperature. The resulting crystals were filtered off and washed with N,N-dimethylformamide. The filtrate was poured into Water (500 ml). The resulting precipitates were collected by filtration, washed with water and dried in vacuo to give 7-chloro-2-(5-hydroxybenzofuran-2-yl)quinoline (12.1 g).

Aufarbeitung

  1. additionwas added at ambient temperature
  2. customAfter the solvent was removed under reduced pressure
  3. stirringAfter the resulting suspension was stirred at ambient temperature for 1 hour
  4. filtrationthe precipitates were collected by filtration
  5. washwashed with water
  6. customdried in vacuo
  7. customto give crude material (15 g)
  8. customto stand at ambient temperature
  9. filtrationThe resulting crystals were filtered off
  10. washwashed with N,N-dimethylformamide
  11. additionThe filtrate was poured into Water (500 ml)
  12. customThe resulting precipitates
  13. filtrationwere collected by filtration
  14. washwashed with water
  15. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b8d328b9b4e74ba1a3c0ce00852afc54
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05661159

Notizen zur Reaktion

Wird geladen…