Methyl 6-chloropyridine-3-carboxylate → HCID 178498148, compound

HRID 744054Notes

Reaction equation

HRID 744054 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.Cl[C:10]1[N:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1.C(=O)(O)[O-].[K+]>O1CCCC1>[NH:6]1[CH:5]=[C:4]([CH2:3][CH2:2][NH:1][C:10]2[CH:11]=[CH:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:15]=2)[N:8]=[CH:7]1

Participants

5

Reactant 3

HCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 516893Potassium BicarbonateHCID 178419017HCID 178419017, compound

Product 1

HCID 178498148HCID 178498148, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.5 g (4.5 mmol) of histamine and 0.77 g (4.5 mmol) of 6-chloro-3-carbomethoxypyridine are stirred with potassium bicarbonate in 20 ml of tetrahydrofuran at 21° C. for 24 h and then heated at reflux for 24 h. The mixture is evaporated and the white solid residue is chromatographed through silica gel, using a chloroform/methanol (4/1) mixture as eluent. The fractions containing the pure product are combined and evaporated and the resulting oily residue is treated with a methanol solution of oxalic acid. Addition of ether provides the title compound in the form of the oxalate salt, M.p.: 209°-210° C. C12H14N4O2.1.7C2H2O4

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. customThe mixture is evaporated
  4. customthe white solid residue is chromatographed through silica gel
  5. additionThe fractions containing the pure product
  6. customevaporated
  7. additionthe resulting oily residue is treated with a methanol solution of oxalic acid
  8. additionAddition of ether

Sources & evidence

ORD record
ord-6040f08aaa7a4dfeb9677c44730c69f2
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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