Hydrochloric Acid → HCID 70872693, compound

HRID 1616501Notes

Reaction equation

HRID 1616501 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([C:10]#[N:11])[C:5](=[O:9])[NH:6][C:7]=1[CH3:8].[BH4-].[Na+].Cl>CO>[NH2:11][CH2:10][C:4]1[C:5](=[O:9])[NH:6][C:7]([CH3:8])=[C:2]([Br:1])[C:3]=1[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7377525-Bromo-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrileHCID 4311764Sodium borohydride

Product 1

HCID 70872693HCID 70872693, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 5-bromo-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (1 g, 4.44 mmol) and NiCl2.6H2O (0.21 g, 0.89 mmol) in methanol at 0° C., NaBH4 (0.68 g, 17.78 mmol) was added portion wise. Reaction mixture was then stirred at rt for overnight period. On completion, it was acidified using 3N HCl and stirred at rt for 3 h. Solvent was removed under reduced pressure. Residue was washed with diethyl ether and basified with aq. NH4OH. Compound was extracted in 10% MeOH in DCM and dried over anhydrous Na2SO4 to give the title compound (0.96 g, 94%) which was used as such for coupling reaction.

Workup

  1. customReaction mixture
  2. stirringstirred at rt for 3 h
  3. customSolvent was removed under reduced pressure
  4. washResidue was washed with diethyl ether and basified with aq. NH4OH
  5. extractionCompound was extracted in 10% MeOH in DCM
  6. dry with materialdried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-94527e69b7b2463989b5355be62b4e9d
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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