Sodium hydride → N-Methyl-N-[4-picolyl]formamide
Reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][CH:3]=1.[CH3:10][NH:11][CH:12]=[O:13].[H-].[Na+]>>[CH3:10][N:11]([CH2:8][C:5]1[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=1)[CH:12]=[O:13]Participants
4
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 TMF 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 CH2 Cl2 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 CH2 Cl2 /MeOH. The title compound was obtained as a pale yellow oil (10.5 g, 76%): ESMS (m/z): 151 (M+ +H).
Workup
- customwas quenched with ice water
- custompartitioned between CH2 Cl2 and H2O
- extractionThe organic extract
- washwas washed with aqueous NaCl
- dry with materialdried over MgSO4
- customThe solvent was removed in vacuo
- customthe residue was purified by flash chromatography
- washeluting with 50:1 CH2 Cl2 /MeOH
Sources & evidence
- ORD record
- ord-00f8d441c27843f18147b91e381c2f68
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05686455
Reaction notes
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