Potassium Carbonate → 2-Chloro-4-[2-(dimethylamino)ethoxy]benzaldehyde
Reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Cl.Cl[CH2:13][CH2:14][N:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 115 °C
Procedure
A suspension of 2-chloro-4-hydroxybenzaldehyde (234 mg, 1.49 mmol), (2-chloroethyl)dimethylamine hydrochloride (536 mg, 3.72 mmol), potassium carbonate (514 mg, 3.72 mmol), and tetrabutylammonium iodide (55 mg, 0.15 mmol) in 4.0 mL of acetonitrile was stirred at 115° C. overnight in a sealed tube. After the reaction mixture was diluted with water, the solution was extracted with ethyl acetate. The extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (chloroform/methanol=99/1 to 94/6) to obtain the title compound as a brown oil (137 mg, 40%).
Workup
- extractionthe solution was extracted with ethyl acetate
- washThe extract was washed with brine
- dry with materialdried over MgSO4
- filtrationAfter filtration
- concentrationthe filtrate was concentrated in vacuo
- customthe residue was purified by silica gel column chromatography (chloroform/methanol=99/1 to 94/6)
Sources & evidence
- ORD record
- ord-d944dde7cd32405ab1fbca676b814217
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552220B2
Reaction notes
Loading…