Sodium → HCID 57969009, compound

HRID 372211Notes

Reaction equation

HRID 372211 reaction equation
C(N1CCCC1C[NH:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[N:13][C:12]=1Cl)C.[CH3:20][O-:21].[Na+].[Na]>CO>[CH3:20][O:21][C:12]1[N:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:10]([NH2:9])=[O:19]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 12905273HCID 12905273, compound

Product 1

HCID 57969009HCID 57969009, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

10.5 g (0.33 mole) of N-[(1-ethyl-2-pyrrolidinyl)-methyl]-2,6-dichloronicotinamide are dissolved in 50 ml of absolute methanol and to this solution is added dropwise a sodium methoxide solution prepared from 0.75 g (0.33 mole) of sodium and 100 ml of absolute methanol in the course of 90 minutes at 40°-45° C. The reaction mixture is kept for 1 hour at 40°-45° C and the methanol is thereafter evaporated in vacuo to a volume of 50 ml. The concentrate is poured onto ice-water, saturated with potassium carbonate and extracted twice with benzene. The organic phases are dried over magnesium sulphate and the solvent is then evaporated in vacuo. The oily residue is chromatographed through a column of basic silica gel with benzene to which 0.5% of methanol is added. Pure N-[1-ethyl-2-pyrrolidinyl)-methyl]-2-methoxy-6-chloronicotinamide is obtained as an oil.

Workup

  1. customthe methanol is thereafter evaporated in vacuo to a volume of 50 ml
  2. additionThe concentrate is poured onto ice-water, saturated with potassium carbonate
  3. extractionextracted twice with benzene
  4. dry with materialThe organic phases are dried over magnesium sulphate
  5. customthe solvent is then evaporated in vacuo
  6. customThe oily residue is chromatographed through a column of basic silica gel with benzene to which 0.5% of methanol
  7. additionis added

Sources & evidence

ORD record
ord-9595ef574a91434490dbe651646331e7
Source dataset
uspto-grants-1978_05
Patent number
US04089960

Reaction notes

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