Methanol → Dimethyl pyridine-2,4-dicarboxylate

HRID 1778319Notes

Reaction equation

HRID 1778319 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[N:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][C:8]=1[C:16]([OH:18])=O.[CH3:19][OH:20].[C:21]([O-])(O)=O.[Na+]>ClCCl.O.O>[CH3:19][O:20][C:16]([C:8]1[CH:9]=[C:10]([C:13]([O:15][CH3:21])=[O:14])[CH:11]=[CH:12][N:7]=1)=[O:18]

Participants

7

Reactant 4

HCID 887MethanolHCID 103652,4-Pyridinedicarboxylic acidHCID 24819Phosphorus pentachlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 254545Dimethyl pyridine-2,4-dicarboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 447138Water dimerSolvent

Procedure

PCl5 (39 g; 0.186 mol; 3 eq) and pyridine-2,4-dicarboxylic acid (11.5 g; 6.2×10−2 mol) are introduced into a 500 mL flask. The mixture is stirred at ambient temperature for 45 minutes: it forms a green liquid. It is then diluted with dichloromethane (80 mL) then methanol is added (20 mL) with caution. The whole is poured into water H2O (300 mL) containing 60 g of NaHCO3, the aqueous phase is washed with dichloromethane (4×50 mL) and the organic phase is washed with 1M Na2CO3 (2×50 mL). The crude product is purified by flash chromatography (eluent: 75:25 AcOEt/cyclohexane).

Workup

  1. washthe aqueous phase is washed with dichloromethane (4×50 mL)
  2. washthe organic phase is washed with 1M Na2CO3 (2×50 mL)
  3. customThe crude product is purified by flash chromatography (eluent: 75:25 AcOEt/cyclohexane)

Sources & evidence

ORD record
ord-d9f6db5fe02f4b4f8ed99e8752455f49
Source dataset
uspto-grants-2016_02
Patent number
US09266902B2

Reaction notes

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