Ethylenediaminetetraacetic Acid → 4-Methoxy-2-methylpyridine

HRID 273326

Reaction equation

HRID 273326 reaction equation
[Cl-].C[Zn+].Cl[C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][N:6]=1.[CH2:13](N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C([O-])([O-])=O.[K+].[K+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:13])[CH:10]=1

Participants

7

Reactant 4

HCID 6049Ethylenediaminetetraacetic AcidHCID 11430Potassium CarbonateHCID 19911282-Chloro-4-methoxypyridineHCID 178477797HCID 178477797, compound

Product 1

HCID 47377584-Methoxy-2-methylpyridineYield 50%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Methylzinc chloride in THF (2 M, 10.489 mL, 21 mmol) was added to a solution of 2-chloro-4-methoxypyridine (0.500 g, 3.48 mmol) and Pd(PPh3)4 (0.161 g, 0.14 mmol) in THF (10 mL). The mixture was refluxed for 40 h and then poured into an aqueous solution (10 mL) containing ethylenediaminetetraacetic acid (1.5 g). The resulting mixture was neutralized with K2CO3 and extracted with Et2O. The organic layer was concentrated to give a residue, which was purified on a silica gel column eluting with MeOH:EtOAc (1:10) to give 4-methoxy-2-methylpyridine (0.213 g, 50.0%).

Workup

  1. temperatureThe mixture was refluxed for 40 h
  2. extractionextracted with Et2O
  3. concentrationThe organic layer was concentrated
  4. customto give a residue, which
  5. customwas purified on a silica gel column
  6. washeluting with MeOH:EtOAc (1:10)

Sources & evidence

ORD record
ord-e810fdf5a0ca4f1d9c55403b4f5a9099
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Linked notes

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