Sodium borohydride → HCID 22935720, compound

HRID 1352510Notes

Reaction equation

HRID 1352510 reaction equation
[C:1]1([N:7]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)[C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.[Ni](Cl)Cl>[C:1]1([N:7]([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH2:13][CH2:12]2)[C:8](=[O:10])[CH3:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22935737HCID 22935737, compound

Product 1

HCID 22935720HCID 22935720, compoundYield 18.7%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-phenyl-N-quinolin-4-ylacetamide (2 g) and Nickel dichloride (7.6 mmol) in methanol, cooled at 0° C., was added sodium borohydride (20 eq). The solution was then stirred overnight, at room temperature. The solvent was removed to give an amorphous materiel, which is crystallized in diethyl ether. After fitration, dichloromethane was added and the solution was washed with water. The organic layer was separated and dried over sodium sulfate. The solvent was removed to obtain an amorphous material. The product was purified by chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (95:5) as eluent to give a N-phenyl-N-1,2,3,4-tetrahydroquinolin-4-ylacetamide (380 mg).

Workup

  1. customThe solvent was removed
  2. customto give an amorphous materiel, which
  3. customis crystallized in diethyl ether
  4. additionAfter fitration, dichloromethane was added
  5. washthe solution was washed with water
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed
  9. customto obtain an amorphous material
  10. customThe product was purified by chromatography on silica gel using
  11. additiona mixture of cyclohexane and ethyl acetate (95:5) as eluent

Sources & evidence

ORD record
ord-cddad48ea2f848bf8d4936adf9c05c15
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

Loading…