Dimethylformamide → HCID 58668622, compound

HRID 2054460Notes

Reaction equation

HRID 2054460 reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][N:7]=1)=[O:4].CN(C)[CH:22]=[O:23]>C1COCC1>[CH:22]([C:11]1[C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:19])([CH3:18])[CH3:1])=[N:7][CH:8]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1)=[O:23]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 47342541HCID 47342541, compound

Product 1

HCID 58668622HCID 58668622, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2,2-dimethyl-N-(5-phenylpyridin-2-yl)propanamide (2.5 g, 9.83 mmol) was dissolved in 80 mL of dry THF and cooled to 0° C. N-Butyl lithium (2.5 M in hexanes) (9.8 mL, 24.57 mmol) was added slowly. The reaction mixture was stirred at 0° C. for 2 hours and then N,N-dimethylformamide (3.6 g, 49.15 mmol) was added. The reaction mixture was removed from the cold bath and allowed to warm to room temperature. After 30 minutes the reaction was quenched with water. The mixture was extracted with EtOAc and dried over MgSO4. The solvent was removed and the residue was chromatographed on silica gel eluting with hexanes/ethyl acetate (2:1) to afford N-(3-formyl-5-phenylpyridin-2-yl)-2,2-dimethylpropanamide (1.87 g).

Workup

  1. customThe reaction mixture was removed from the cold bath
  2. temperatureto warm to room temperature
  3. customAfter 30 minutes the reaction was quenched with water
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed
  7. customthe residue was chromatographed on silica gel eluting with hexanes/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-fb7edf70d5bb42998eb6cf93072fbe3d
Source dataset
uspto-grants-2008_02
Patent number
US07329678B2

Reaction notes

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