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

HRID 908826

Reaction equation

HRID 908826 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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.

Sources & evidence

ORD record
ord-248cea8897d74b6b92a4fe823b80b4d2
Source dataset
uspto-grants-2011_09
Patent number
US08017625B2

Linked notes

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