Sodium borohydride → HCID 90387286, compound

HRID 1476804Notes

Reaction equation

HRID 1476804 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:12](OC)=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:3]=[C:4]([CH2:12][OH:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 903869511627603-62-6

Product 1

HCID 90387286HCID 90387286, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-chloroisoquinoline-1-carboxylate (5.1 g, 23.0 mmol) in MeOH (50 mL) was added NaBH4 (2.17 g, 57.5 mmol). The reaction mixture was stirred at RT for 2 hours. The reaction was quenched with saturated aqueous NH4Cl and the mixture was extracted with EtOAc. The organic layer was separated and dried over Na2SO4, and the solvent was evaporated under reduced pressure to give the title compound as a yellow solid (3.94 g, 88%). ESI-MS m/z [M+H]+ 194.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionthe mixture was extracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-24e5c77f68674d37b8fac3e597e323d9
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

Loading…