Sodium Bicarbonate → rac-5-{[2-(5-Fluoro-2-hydroxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylic acid

HRID 875328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875328
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:23]C)=[C:6]([CH2:8][CH2:9][NH:10][CH:11]2[CH2:20][CH2:19][CH2:18][C:17]3[N:16]=[C:15](C#N)[CH:14]=[CH:13][C:12]2=3)[CH:7]=1.[C:25](=[O:28])(O)[O-:26].[Na+]>Br.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:23])=[C:6]([CH2:8][CH2:9][NH:10][CH:11]2[CH2:20][CH2:19][CH2:18][C:17]3[N:16]=[C:15]([C:25]([OH:26])=[O:28])[CH:14]=[CH:13][C:12]2=3)[CH:7]=1

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 89940804rac-5-{[2-(5-Fluoro-2-methoxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carbonitrile

Produkt 1

HCID 89940808rac-5-{[2-(5-Fluoro-2-hydroxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 260Hydrogen BromideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

72.8 g (223.73 mmol) of rac-5-{[2-(5-fluoro-2-methoxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carbonitrile were taken up in 360 ml of hydrobromic acid (48% in water) and initially stirred at boiling point for 12 h, then cooled to room temperature and allowed to stand at this temperature overnight. The reaction solution was then diluted with 400 ml of water and adjusted to pH 6 using saturated sodium bicarbonate solution. The crystals formed were filtered off with suction, washed with water and dried under reduced pressure at 50° C. This gave 59 g (178.59 mmol, 80% of theory) of the target compound.

Aufarbeitung

  1. customfor 12 h
  2. customto stand at this temperature overnight
  3. customThe crystals formed
  4. filtrationwere filtered off with suction
  5. washwashed with water
  6. customdried under reduced pressure at 50° C

Quellen und Nachweise

ORD-Eintrag
ord-84345edf12d04a32a106081dbec76061
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981104B2

Notizen zur Reaktion

Wird geladen…