Dimethylformamide → 2-Chloro-5-methylpyridine-3-carbaldehyde
Reaction equation
CN([CH:4]=[O:5])C.[CH2:6]([N:13](/C=C/C)C(=O)C)[C:7]1[CH:12]=CC=[CH:9][CH:8]=1.[C:20]([Cl:23])(Cl)=O>>[Cl:23][C:20]1[C:9]([CH:4]=[O:5])=[CH:8][C:7]([CH3:12])=[CH:6][N:13]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
DMF (2.86 mL, 37.0 mmol) was added slowly over 2 minutes to an ice-cold solution of N-benzyl-N—((E)-propenyl)-acetamide (1.0 g, 5.3 mmol) and phosgene (20% in toluene; 18.3 mL, 37.0 mmol). After stirring for 30 minutes at 0° C., the ice bath was removed, and the reaction was stirred at room temperature for 2 hours, and then heated to 75° C. for 4.5 hours. The mixture was poured over ice and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.
Workup
- customthe ice bath was removed
- stirringthe reaction was stirred at room temperature for 2 hours
- temperatureheated to 75° C. for 4.5 hours
- additionThe mixture was poured over ice
- extractionextracted with CH2Cl2
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customthe residue was purified by silica gel chromatography (0-50% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-a649daeb1e954ae581ea45ca6a209bd6
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378107B2
Reaction notes
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