Sodium Hydroxide → HCID 86723763, compound

HRID 577534Notes

Reaction equation

HRID 577534 reaction equation
C([O:4][C:5]1[C:14]2[C:9](=[C:10]([Br:20])[CH:11]=[C:12]([O:16][CH:17]([CH3:19])[CH3:18])[C:13]=2[CH3:15])[CH:8]=[CH:7][N:6]=1)(=O)C.[OH-].[Na+]>CO>[Br:20][C:10]1[CH:11]=[C:12]([O:16][CH:17]([CH3:18])[CH3:19])[C:13]([CH3:15])=[C:14]2[C:9]=1[CH:8]=[CH:7][NH:6][C:5]2=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86723764HCID 86723764, compound

Product 1

HCID 86723763HCID 86723763, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-8-methyl-7-(propan-2-yloxy)isoquinolin-1-yl acetate (108 g, 0.28 g, 0.83 mmol) in MeOH (2 mL) was added 1M NaOH (2 mL). The reaction mixture was refluxed for 1 hour, then concentrated under vacuum. The residue was diluted in water and the pH was adjusted to 4-5 with 1M HCl. The solution was extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine (2×10 mL), dried over Na2SO4, filtered, and concentrated under vacuum to give 5-bromo-8-methyl-7-(propan-2-yloxy)isoquinolin-1(2H)-one (108h, 0.21 g, 86%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. concentrationconcentrated under vacuum
  3. additionThe residue was diluted in water
  4. extractionThe solution was extracted with EtOAc (3×10 mL)
  5. washThe combined organic layers were washed with brine (2×10 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a0f8c6b248414c0bac729b5e63167c4c
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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