Sodium Chlorite → 1-Methoxy-5-methylisoquinolin-4-carboxylic acid

HRID 1470459Notes

Reaction equation

HRID 1470459 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[C:6]([CH:14]=[O:15])=[CH:5][N:4]=1.[O-:16]Cl=O.[Na+]>C(#N)C.O>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[C:6]([C:14]([OH:16])=[O:15])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 23668197Sodium ChloriteHCID 247661931-Methoxy-5-methylisoquinolin-4-carbaldehyde

Product 1

HCID 682818821-Methoxy-5-methylisoquinolin-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a stirred solution of 1-methoxy-5-methylisoquinolin-4-carbaldehyde (Intermediate-7) (2 g, 10 mmol) in ACN—H2O (120 mL, 1:1) was added, NaClO2 (5.4 g, 59.7 mmol), NaH2PO4 (5.5 g, 40 mmol) and the mixture was stirred at RT overnight. It was then extracted with EtOAc (3×150 mL), dried over Na2SO4, filtered and concentrated to give the desired acid derivative (1.2 g, 56%).

Workup

  1. extractionIt was then extracted with EtOAc (3×150 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-da50407e99d44be6a8dd3153de24f8e9
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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