Sodium → Methyl 6-chloro-2-methoxynicotinate

HRID 372209Notes

Reaction equation

HRID 372209 reaction equation
[CH3:1][O-:2].[Na+].[Na].Cl[C:6]1[N:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]>CO>[CH3:1][O:2][C:6]1[N:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 11106516Methyl 2,6-dichloropyridine-3-carboxylate

Product 1

HCID 10560015Methyl 6-chloro-2-methoxynicotinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A sodium methoxide solution prepared from 3.46 g (0.15 mole) of sodium and 150 ml of absolute methanol is added dropwise at 40° C in the course of 1 hour to a solution of 312 g (0.15 mole) of methyl 2,6-dichloronicotinate in 100 ml of methanol. The reaction mixture is refluxed for 3 hours and the solvent is then evaporated in vacuo. The dry residue is triturated with methylene chloride, the undissolved constituents are filtered off and the filtrate is evaporated in vacuo to dryness. The crystallised residue is recrystallised from petroleum ether to yield pure methyl 2-methoxy-6-chloronicotinate with a melting point of 68°-69° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hours
  2. customthe solvent is then evaporated in vacuo
  3. customThe dry residue is triturated with methylene chloride
  4. filtrationthe undissolved constituents are filtered off
  5. customthe filtrate is evaporated in vacuo to dryness
  6. customThe crystallised residue is recrystallised from petroleum ether

Sources & evidence

ORD record
ord-a22f6535525540718097309ae6f0865f
Source dataset
uspto-grants-1978_05
Patent number
US04089960

Reaction notes

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