Sodium Hydroxide → 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid

HRID 351571Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351571
C([O:3][C:4]([C:6]1[C:16]2=[C:17]3[C:12](=[CH:13][CH:14]=[CH:15]2)[CH2:11][CH2:10][CH2:9][N:8]3[CH:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C.O>[C:6]1([C:4]([OH:5])=[O:3])[C:16]2=[C:17]3[C:12](=[CH:13][CH:14]=[CH:15]2)[CH2:11][CH2:10][CH2:9][N:8]3[CH:7]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 20729414Ethyl 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylate

Produkt 1

HCID 225568865,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

To a solution of 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid ethyl ester (31 g, 0.14 mol) in ethanol (200 mL) and water (70 mL) was added 5 N aqueous sodium hydroxide(60 mL, 0.3 mol) and the resulting mixture stirred at reflux for 3 hours. The reaction mixture was cooled to 20-24° C., diluted with water (2 L) and washed with dichloromethane(2×200 mL) and diethyl ether (1×200 mL). The aqueous layer was filtered through Celite and the filtrate was acidified with conc. HCl (25 mL) to precipitate the product. The solid was filtered, washed with water (200 mL), and dried in vacuo to give 23.2 g (85%) of the desired compound as a light yellow solid.

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. washwashed with dichloromethane(2×200 mL) and diethyl ether (1×200 mL)
  3. filtrationThe aqueous layer was filtered through Celite
  4. customto precipitate the product
  5. filtrationThe solid was filtered
  6. washwashed with water (200 mL)
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bf93516ce3db42ed84e196223a0db2f6
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743785B2

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