Potassium Hydroxide → 5-Bromoisoquinoline-4-carboxylic acid

HRID 1470483Notes

Reaction equation

HRID 1470483 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:12]([O:14]C)=[O:13])=[CH:5][N:6]=[CH:7]2.[OH-].[K+]>CO.O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:12]([OH:14])=[O:13])=[CH:5][N:6]=[CH:7]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 68281832Methyl 5-bromoisoquinoline-4-carboxylate

Product 1

HCID 682819235-Bromoisoquinoline-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of methyl 5-bromoisoquinolin-4-carboxylate (Intermediate-16) (10.1 g, 38.0 mmol) in MeOH (50 mL) was added, KOH (21.3 g, 380 mmol) dissolved in water (50 mL) and the reaction mixture was heated to 70° C. for 3 h. Then it was concentrated, diluted with water and washed with Et2O (100 mL×3). The aqueous layer was acidified with 2N HCl (pH=3) and the white solid obtained was filtered to yield the desired acid derivative 6.0 g (62.7%).

Workup

  1. concentrationThen it was concentrated
  2. additiondiluted with water
  3. washwashed with Et2O (100 mL×3)
  4. customthe white solid obtained
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-f1868970be9448e6984a1bf06e3ae4ea
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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