Sodium Hydroxide → 4'-METHYL-2,2'-BIPYRIDINE-4-CARBOXYLIC ACID

HRID 1595931Notes

Reaction equation

HRID 1595931 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[C:12]([CH:14]=[O:15])[CH:11]=[CH:10][N:9]=2)[CH:3]=1.[OH-:16].[Na+]>CCO.O.[N+]([O-])([O-])=O.[Ag+]>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[CH:11]=[CH:10][N:9]=2)[CH:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 111939724'-Methyl[2,2'-bipyridine]-4-carbaldehyde

Product 1

HCID 111276214'-METHYL-2,2'-BIPYRIDINE-4-CARBOXYLIC ACIDYield 77%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 4′-methyl-2,2′-bipyridine-4-carboxaldehyde (3.5 g, 15 mmol) in 95% EtOH (150 ml) was added a solution of AgNO3 (3.15 g) in water (32 ml). The suspension was stirred rapidly and 1M NaOH (79 ml) solution was added dropwise over 20 min to form Ag2O. The dark black solution was stirred for an additional 15 hrs. EtOH was removed by rotary evaporator and filtred to remove Ag2O and unreacted metallic Ag. The residue was washed with 1.3M NaOH (2*20 ml) and H2O 20 ml. The combined basic filterate was extracted with DCM to remove unreacted aldehyde and adjusted to pH 3.5 with 1:1(v/v) 4N HCl/AcOH to afford white compound. After keeping overnight at −10° C. the compound was collected and dried to afford pure compound 2.9 g (77%). Mass Spect. (FAB) MW 215 [M+]; NMR assigned.

Workup

  1. customto form Ag2O
  2. stirringThe dark black solution was stirred for an additional 15 hrs
  3. customEtOH was removed by rotary evaporator
  4. customto remove Ag2O and unreacted metallic Ag
  5. washThe residue was washed with 1.3M NaOH (2*20 ml) and H2O 20 ml
  6. extractionThe combined basic filterate was extracted with DCM
  7. customto remove unreacted aldehyde
  8. customto afford white compound
  9. customthe compound was collected
  10. customdried

Sources & evidence

ORD record
ord-c4464a268344461dad54d7c4454bf853
Source dataset
uspto-grants-2001_09
Patent number
US06288221B1

Reaction notes

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