2,5-Pyridinedicarboxylic acid → HCID 53805562, compound

HRID 2255073Notes

Reaction equation

HRID 2255073 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[CH:4]=[CH:3][C:2]=1[C:10]([OH:12])=[O:11].S(Cl)(Cl)=O.[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([N+:26]([O-:28])=[O:27])=[C:22]([CH:25]=1)[CH2:23]O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N:1]1[CH:6]=[C:5]([C:7]([O:9][CH2:23][C:22]2[CH:25]=[C:18]([CH3:17])[CH:19]=[CH:20][C:21]=2[N+:26]([O-:28])=[O:27])=[O:8])[CH:4]=[CH:3][C:2]=1[C:10]([O:12][CH2:23][C:22]1[CH:25]=[C:18]([CH3:17])[CH:19]=[CH:20][C:21]=1[N+:26]([O-:28])=[O:27])=[O:11]

Participants

6

Reactant 4

HCID 74932,5-Pyridinedicarboxylic acidHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 568847(5-Methyl-2-nitrophenyl)methanol

Product 1

HCID 53805562HCID 53805562, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Analogously to Example 1, 5 g of pyridine-2,5-dicarboxylic acid are converted into the acid chloride with 40 ml of thionyl chloride in 30 ml of methylene chloride and this is reacted with 10 g of 5-methyl-2-nitro-benzyl alcohol in 50 ml of methylene chloride. The reaction mixture is stirred overnight at room temperature, sodium bicarbonate solution is then added, the mixture is extracted with methylene chloride and the organic phase is dried. After the solvent has been stripped off, the residue is stirred with ethyl acetate, filtered off with suction and recrystallized twice from methylene chloride.

Workup

  1. extractionthe mixture is extracted with methylene chloride
  2. customthe organic phase is dried
  3. stirringthe residue is stirred with ethyl acetate
  4. filtrationfiltered off with suction
  5. customrecrystallized twice from methylene chloride

Sources & evidence

ORD record
ord-8b924f3dd55349bebc181365c19e2fb4
Source dataset
uspto-grants-1993_08
Patent number
US05238948

Reaction notes

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