Hydrochloric Acid → 6-Bromo-2-[(4-methoxyphenyl)methyl]-1(2H)-isoquinolinone

HRID 907258Notes

Reaction equation

HRID 907258 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]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:6](=O)[CH2:5]2.[BH4-].[Na+].Cl>ClCCl.CO>[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]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 575517366-Bromo-2-(4-methoxy-benzyl)-4H-isoquinoline-1,3-dione2×

Product 1

HCID 575517716-Bromo-2-[(4-methoxyphenyl)methyl]-1(2H)-isoquinolinone

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 6-bromo-2-(4-methoxy-benzyl)-4H-isoquinoline-1,3-dione (product of step iii)) (2.6 g) in dichloromethane:methanol (3:1, 80 mL) was added sodium borohydride (1.0 g) portionwise over 2 hours. The reaction mixture was acidified with hydrochloric acid and stirred for 30 minutes. The reaction mixture was evaporated and the residue partitioned between dichloromethane and water. The organic phase was washed with brine, dried, filtered and evaporated. The residue was purified (SiO2, 1:4 ethyl acetate:iso-hexane as eluent) to yield the sub-title compound (1.2 g).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue partitioned between dichloromethane and water
  3. washThe organic phase was washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified (SiO2, 1:4 ethyl acetate:iso-hexane as eluent)

Sources & evidence

ORD record
ord-c94718cf9d614c0eb0e1dc0b1e645870
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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