Sodium borohydride → HCID 67324605, compound

HRID 882085Notes

Reaction equation

HRID 882085 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:15]#[N:16])[C:11]=1[N:12]([CH3:14])[CH3:13])[N:8]=[C:7]([CH:17]=[O:18])[CH:6]=[CH:5]2.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:15]#[N:16])[C:11]=1[N:12]([CH3:14])[CH3:13])[N:8]=[C:7]([CH2:17][OH:18])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86683822HCID 86683822, compound

Product 1

HCID 67324605HCID 67324605, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 6-bromo-7-dimethylamino-2-formylquinolin-8-carbonitrile (2.4 g, 7.9 mmol, 1.0 eq) was added to MeOH (20 mL) at 0° C. Sodium borohydride (328 mg, 8.7 mmol, 1.1 eq) was then introduced and the mixture was stirred at room temperature for 1 hour. The solution was quenched with HCl 1 M, ethanol was evaporated and water was added. The solution was extracted with dichloromethane and the organic layer was washed twice with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The 6-bromo-7-dimethylamino-2-(hydroxymethyl)quinoline-8-carbonitrile was obtained as an orange solid (2.4 g, 98%).

Workup

  1. customThe solution was quenched with HCl 1 M, ethanol
  2. customwas evaporated
  3. additionwater was added
  4. extractionThe solution was extracted with dichloromethane
  5. washthe organic layer was washed twice with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5137bcfb1bb044b7a73ced6f2590ce6c
Source dataset
uspto-grants-2015_03
Patent number
US08993767B2

Reaction notes

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