Sodium hydride → N-formyl-N-(pyridin-2-yl)formamide

HRID 2041813Notes

Reaction equation

HRID 2041813 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH:10]=[O:11].[CH:12](OC(=O)C)=[O:13]>C1COCC1>[CH:10]([N:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1)[CH:12]=[O:13])=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75269Acetic-formic anhydrideHCID 3781604N-(pyridin-2-yl)formamide

Product 1

HCID 59583153N-formyl-N-(pyridin-2-yl)formamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (10.8 g, 60 wt %, 0.27 mol) in 50 mL of THF was added dropwise a solution of N-(pyridine-2-yl)formamide (22.4 g, 0.18 mol) in 250 mL of THF. When the addition was complete, the reaction was stirred at room temperature for 30 minutes and then cooled in an ice/salt bath. The acetic formic anhydride ethereal solution from the previous step was added in one portion. The resulting mixture was stirred in the ice bath for 30 minutes and then overnight at room temperature. The mixture was poured into 1 L of ice/water and extracted with 3×250 mL of CH2Cl2. The combined organic extracts were washed with 2×250 mL of H2O, dried and evaporated to give 33.2 g of solid. The crude product was column chromatographed (silica gel) eluting with 100% CH2Cl2 followed by 90:10 CH2Cl2:EtOAc. 14.2 g of product was isolated as a white solid.

Workup

  1. additionWhen the addition
  2. temperaturecooled in an ice/salt bath
  3. customovernight
  4. customat room temperature
  5. extractionextracted with 3×250 mL of CH2Cl2
  6. washThe combined organic extracts were washed with 2×250 mL of H2O
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-e3f14fc30e2d4ba5a5d5209aee2ee9d2
Source dataset
uspto-grants-2013_11
Patent number
US08586203B2

Reaction notes

Loading…