Sodium Acetate → 6-Bromo-2-(3-hydroxy-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinoline-4-carbaldehyde

HRID 906421Notes

Reaction equation

HRID 906421 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15]Cl)[CH:6]=[C:5]2[CH:19]=[O:20].C([O-])(=[O:23])C.[Na+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][OH:23])[CH:6]=[C:5]2[CH:19]=[O:20]

Participants

4

Reactant 2

HCID 517045Sodium Acetate2×HCID 866409616-Bromo-2-(3-chloro-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinoline-4-carbaldehyde

Product 1

HCID 866409686-Bromo-2-(3-hydroxy-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinoline-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 6-bromo-2-(3-chloro-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinoline-4-carbaldehyde (Example 26c, 20 g) in DMSO (140 mL) was treated with sodium acetate (55 g) under nitrogen. The resulting mixture was stirred at 135° C. for 48 h during which more sodium acetate was added after 6 h (55 g), 24 h (55 g) then 30 h (22.5 g).

Workup

  1. additionwas added after 6 h (55 g), 24 h (55 g)
  2. custom30 h (22.5 g)

Sources & evidence

ORD record
ord-4f9145a0ce324abd8c91727f764cfa17
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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