Sodium borohydride → HCID 66606820, compound

HRID 661834Notes

Reaction equation

HRID 661834 reaction equation
[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([N:8]2[C:17](=[O:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([N:8]2[CH:17]([OH:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 68746412HCID 68746412, compound

Product 1

HCID 66606820HCID 66606820, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step 2 A suspension of 2-(3-bromo-2-methylphenyl)isoquinoline-1,3(2H,4H)-dione (630 mg, 1.908 mmol) in methanol (100 mL) was treated with sodium borohydride (217 mg, 5.72 mmol) at rt. After 1.5 h, additional sodium borohydride (120 mg) was added. After 7 h, the mixture was concentrated and the residue was partitioned between water and DCM. The organic phase was dried and concentrated to give 2-(3-bromo-2-methylphenyl)-3-hydroxy-3,4-dihydroisoquinolin-1(2H)-one as a light yellow foam (600 mg, 95%), used without further purification. Mass spectrum m/z 332, 334 (M+H)+.

Workup

  1. waitAfter 7 h
  2. concentrationthe mixture was concentrated
  3. customthe residue was partitioned between water and DCM
  4. customThe organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e67c627a8b3c42afaf82a0f58ba486ca
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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