2,2'-Bipyridine → HCID 58965485, compound

HRID 363733Notes

Reaction equation

HRID 363733 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.C(NCC)C.[CH2:18]([N:20]([CH2:23][CH3:24])[CH2:21]C)[CH3:19].[C:25](=O)([O-:27])[O-:26].[Na+].[Na+].S(Cl)(Cl)=[O:32]>C1(C)C=CC=CC=1>[CH2:18]([N:20]([CH2:23][CH3:24])[C:21]([C:4]1[CH:5]=[CH:6][N:1]=[C:2]([C:7]2[CH:12]=[C:11]([C:25]([OH:27])=[O:26])[CH:10]=[CH:9][N:8]=2)[CH:3]=1)=[O:32])[CH3:19]

Participants

7

Reactant 5

HCID 14742,2'-BipyridineHCID 8021DiethylamineHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 24386Thionyl Chloride

Product 1

HCID 58965485HCID 58965485, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,2'-Bipyridine, 4,4'-dicarboxylic acid (1.0 g, 4.1 mol) is refluxed in 10 mL of thionyl chloride for 5 hours. The thionyl chloride is removed under reduced pressure, and added to 100 mL of toluene. The mixture is brought to a boil and filtered (gravity) into a cold stirring solution containing diethylamine (600 mg, 8.2 mmol), triethylamine (836 mg, 8.3 mmol) and 50 mL of toluene. The resulting solution is allowed to stir at room temperature for 30 minutes. The solution is poured into 100 mL of saturated sodium carbonate solution, and the layers are separated. The aqueous phase is extracted twice with 50 mL portions of chloroform. The extracts are combined with the toluene, and the volume reduced to about 10 mL by distillation. Heptane (50 ml) is added to the residue, and the resulting solid is filtered giving 2,2'-bipyridine-4,4'-dicarboxylic acid, N,N diethyl amide, as a low melting solid (500 mg).

Workup

  1. customThe thionyl chloride is removed under reduced pressure
  2. additionadded to 100 mL of toluene
  3. filtrationfiltered (gravity) into a cold stirring solution
  4. customthe layers are separated
  5. extractionThe aqueous phase is extracted twice with 50 mL portions of chloroform
  6. distillationthe volume reduced to about 10 mL by distillation
  7. additionHeptane (50 ml) is added to the residue
  8. filtrationthe resulting solid is filtered

Sources & evidence

ORD record
ord-806c5a70b578408a96c524e10c3c5832
Source dataset
uspto-grants-1999_02
Patent number
US05874587

Reaction notes

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