Hydrochloric Acid → N-Methyl-N-[4-picolyl]formamide

HRID 479774Notes

Reaction equation

HRID 479774 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7]Cl)=[CH:3][CH:2]=1.Cl.[CH3:10][NH:11][CH:12]=[O:13].[H-].[Na+]>C1COCC1>[CH3:10][N:11]([CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[CH:12]=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 31254N-MethylformamideHCID 745714-(Chloromethyl)pyridine

Product 1

HCID 15893405N-Methyl-N-[4-picolyl]formamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-picolyl chloride.HCl (15 g, 91.4 mmol) and N-methylformamide (53.4 mL, 914 mmol) in 300 mL of THF was added 80% NaH in mineral oil (5.48 g, 183 mmol). After stirring at rt for 18 h the mixture was quenched with ice water and partitioned between CH2Cl2 and H2O. The organic extract was washed with aqueous NaCl and dried over MgSO4. The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with 50:1 CH2Cl2/MeOH. The title compound was obtained as a pale yellow oil (10.5 g, 76%): ESMS (m/z): 151 (M++H).

Workup

  1. customwas quenched with ice water
  2. custompartitioned between CH2Cl2 and H2O
  3. extractionThe organic extract
  4. washwas washed with aqueous NaCl
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography
  8. washeluting with 50:1 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-26c807b4e5714edb813631b2ac84c12f
Source dataset
uspto-grants-2003_11
Patent number
US06645989B2

Reaction notes

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