Sodium Hydroxide → 1-Bromo-4-hydroxy-7-phenoxyisoquinoline-3-carboxylic acid

HRID 908717Notes

Reaction equation

HRID 908717 reaction equation
C([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:26])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])CCC.[OH-].[Na+]>CCO>[Br:26][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[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 86595463Butyl 1-bromo-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 860145231-Bromo-4-hydroxy-7-phenoxyisoquinoline-3-carboxylic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-Bromo-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester (3.52 g, 8.45 mmol; Example A-65 e) aqueous 2N NaOH (50 ml, 100 mmol) and EtOH (50 ml) was refluxed with stirring for 2 h. Then the solution was concentrated in vacuo to ½ of its volume, diluted with water (180 ml), and was acidified by addition of aqueous 6N HCl (20 ml). After stirring at ambient temperature for 30 min the resulting suspension was submitted to vacuum filtration. The filter cake was washed thoroughly with water and dried in vacuo at 70° C. to give the title compound as a white solid (3.05 g); 1H NMR (DMSO-d6): δ=8.33 (d, 1H), 7.20 to 7.61 (m, 7H).

Workup

  1. temperaturewas refluxed
  2. concentrationThen the solution was concentrated in vacuo
  3. additiondiluted with water (180 ml)
  4. additionwas acidified by addition of aqueous 6N HCl (20 ml)
  5. stirringAfter stirring at ambient temperature for 30 min the resulting suspension
  6. filtrationwas submitted to vacuum filtration
  7. washThe filter cake was washed thoroughly with water
  8. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-db1430209a8c459eb6c67996cb687055
Source dataset
uspto-grants-2011_09
Patent number
US08017625B2

Reaction notes

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