Hydrochloric Acid → N-(3-Formyl-2-pyridinyl)-2,2-dimethylpropanamide

HRID 2194506Notes

Reaction equation

HRID 2194506 reaction equation
[C:1]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C([Li])CCC.CN(C)[CH:21]=[O:22].Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH:21]([C:13]1[C:8]([NH:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10515192-(Pivaloylamino)pyridineHCID 178418339Butyllithium

Product 1

HCID 736837N-(3-Formyl-2-pyridinyl)-2,2-dimethylpropanamideYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

11.4 g (64 mmol) of 2-(pivaloylamino)pyridine was dissolved in 50 mL of tetrahydrofuran, and 100 mL (0.16 mol) of 1.6 M normal-butyllithium was added dropwise thereto at −60° C. The mixture was allowed to react for 3 hours at −10° C. To this reaction mixture, 14 g (0.19 mol) of N,N-dimethylformamide was added dropwise at −60° C., and the reaction liquid was stirred overnight at room temperature. The reaction mixture was poured into ice, and 6 N hydrochloric acid was added thereto to acidify the reaction mixture. Subsequently, potassium carbonate was added to make the reaction mixture alkaline, and the mixture was extracted with ethyl acetate. The organic phase was washed with water, and was dried and concentrated. The residue thus obtained was purified by column chromatography (ethyl acetate:n-hexane=1:4 to 1:0), and thus 6.57 g (yield 50%) of the title compound was obtained as a pale yellow liquid.

Workup

  1. customat −60° C
  2. customto react for 3 hours at −10° C
  3. customthe reaction liquid
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic phase was washed with water
  7. customwas dried
  8. concentrationconcentrated
  9. customThe residue thus obtained
  10. customwas purified by column chromatography (ethyl acetate:n-hexane=1:4 to 1:0)

Sources & evidence

ORD record
ord-5d9a275b6fb145e78c70b500249abdc4
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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