Sodium borohydride → HCID 22677319, compound

HRID 1837458Notes

Reaction equation

HRID 1837458 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][CH:11]=2)[N:7]=[C:6]([C:18]([O:20][CH3:21])=[O:19])[C:5]=1[Cl:22]>CO.ClCCl>[NH2:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=2)[N:7]=[C:6]([C:18]([O:20][CH3:21])=[O:19])[C:5]=1[Cl:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22677344HCID 22677344, compound

Product 1

HCID 22677319HCID 22677319, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Sodium borohydride (112 mg, 3 mmol) was slowly added to a solution of methyl 4-amino-3-chloro-6-(4-formylphenyl)pyridine-2-carboxylate (2.87 g, 9.87 mmol) in methanol/dichloromethane (1:1, 100 mL) cooled by an ice bath. After the addition was complete, the ice bath was removed and the reaction mixture was stirred for 15 minutes and then concentrated. The residue was dissolved in ethyl acetate/water and the organic phase was washed with brine, dried (MgSO4) and concentrated. The residue was purified by column chromatography over silica gel (40% ethyl acetate/hexane) to yield methyl 4-amino-3-chloro-6-(4-hydroxymethylphenyl)pyridine-2-carboxylate (2.5 g 8.54 mmol), mp 138-139° C.

Workup

  1. temperaturecooled by an ice bath
  2. additionAfter the addition
  3. customthe ice bath was removed
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethyl acetate/water
  6. washthe organic phase was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography over silica gel (40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ad54fe21fac74ff2932e05fadcdca382
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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