Sodium Hydroxide → 1-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid

HRID 250447

Reaktionsgleichung

Reaktionsgleichung von HRID 250447
C([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:19])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])CCC.[OH-].[Na+]>CCO>[Br:19][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([OH:7])=[O:5])[N:9]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 860145411-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

Produkt 1

HCID 860146131-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (8.18 g, 25 mmol; Example D-28 a) aqueous 2N NaOH (80 ml, 160 mmol) and EtOH (80 ml) was refluxed with stirring for 2 h. Then the solution was concentrated in vacuo to ½ of its volume, diluted with water (200 ml), and was acidified by addition of concentrated aqueous HCl. After stirring at ambient temperature for 1 h the resulting suspension was submitted to vacuum filtration. The filter cake was washed thoroughly with water and dried in vacuo at 75° C. to give the title compound as a white solid (6.10 g); 1H NMR (DMSO-d6): δ=8.30 to 8.37 (m, 1H), 8.16 to 8.22 (m, 1H), 7.93 to 8.03 (m, 2H).

Aufarbeitung

  1. concentrationThen the solution was concentrated in vacuo
  2. additiondiluted with water (200 ml)
  3. additionwas acidified by addition of concentrated aqueous HCl
  4. stirringAfter stirring at ambient temperature for 1 h the resulting suspension
  5. filtrationwas submitted to vacuum filtration
  6. washThe filter cake was washed thoroughly with water
  7. customdried in vacuo at 75° C.

Quellen und Nachweise

ORD-Eintrag
ord-41dc24e4302e45e7a3ce82cd9384fa73
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863292B2

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