Sodium borohydride → HCID 10381052, compound

HRID 1783312Notes

Reaction equation

HRID 1783312 reaction equation
[Br-].[CH2:2]([N+:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[NH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[CH2:2]([N:9]1[CH2:10][CH:11]=[C:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[NH:17][CH:16]=2)[CH2:13][CH2:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23084711HCID 23084711, compound

Product 1

HCID 10381052HCID 10381052, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-4-(1-oxo-2H-isoquinolin-4-yl)pyridinium bromide (9.0 g) was dissolved in methanol (100 mL), and sodium borohydride (3.7 g) was added in small portions with stirring at room temperature. After the completion of the reaction, the solvent was evaporated. Water was added to the obtained residue, and the mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate, and the solvent was evaporated. Ethyl acetate was added to the obtained residue, and the precipitated crystals were collected by filtration to give 4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-2H-isoquinolin-1-one (6.5 g).

Workup

  1. customAfter the completion of the reaction
  2. customthe solvent was evaporated
  3. additionWater was added to the obtained residue
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was evaporated
  7. additionEthyl acetate was added to the obtained residue
  8. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-9a243f2132184c8ea3a0e69cc8445a07
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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