Hydrochloric Acid → Methyl 2-benzyl-nicotinoylacetate

HRID 1795444Notes

Reaction equation

HRID 1795444 reaction equation
[H-].[Na+].[C:3]([CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>C1COCC1>[CH2:16]([C:5]1[N:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:10])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1086453-Pyridinepropanoic acid, beta-oxo-, methyl ester

Product 1

HCID 66862536Methyl 2-benzyl-nicotinoylacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (300 mg; 60%) is added to the solution of methyl nicotinoylacetate (896 mg, 5 mmol) in THF (15 mL) at 0° C. under argon atmosphere. The reaction mixture is stirred for 15 minutes at the temperature and benzyl bromide (0.36 mL) is added. The reaction mixture is heated at reflux overnight. The reaction mixture is poured into iced 1N HCl and extracted with EtOAc three times. The combined organic extract is washed with brine and dried over MgSO4. Concentration under reduced pressure gives the residue which is purified over column chromatography to afford methyl 2-benzyl-nicotinoylacetate intermediate (389 mg).

Workup

  1. additionis added
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux overnight
  4. extractionextracted with EtOAc three times
  5. extractionThe combined organic extract
  6. washis washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationConcentration under reduced pressure
  9. customgives the residue which
  10. customis purified over column chromatography

Sources & evidence

ORD record
ord-afb0ea8fdbde47f8b885c0bfbd330924
Source dataset
uspto-grants-2006_04
Patent number
US07026491B2

Reaction notes

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