Potassium Carbonate → HCID 60207431, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12].Cl.Cl[CH2:15][CH2:16][CH2:17][NH2+:18][CH3:19].[C:20](=O)([O-])[O-].[K+].[K+]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[O:12][CH2:15][CH2:16][CH2:17][N:18]([CH3:19])[CH3:20]Participants
Conditions
- Temperature
- 120 °C
Procedure
To a solution of 2-methoxy-4-nitrophenol (1.0 g, 5.9 mmol) and 3-chloro-N-methylpropan-1-aminium hydrochloride salt (1.03 g, 6.5 mmol) in N,N-dimethylformide (10 mL), was added potassium carbonate (2.03 g, 14.7 mmol). The resulting reaction mixture was heated at 120° C. for 18 hours. After this time, TLC analysis showed no starting material remaining so the mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried (Na2SO4) and concentrated. The crude residue was purified by silica gel chromatography using a 95:5 mixture of dichloromethane and methanol as eluent to afford the title product as yellow oil (0.8 g, 53% yield). 1H NMR (400 MHz, d6-DMSO) δ: 7.57 (1H, m), 7.44 (1H, m), 7.06 (1H, m), 4.07 (2H, m), 3.81 (3H, s), 3.812 (3H, s), 3.807 (2H, s), 2.33 (2H, m), 2.13 (6H, s), 1.86 (2H, m). MS m/z: 268.26 [M+H]+.
Workup
- customThe resulting reaction mixture
- customwas quenched with water
- extractionextracted with ethyl acetate
- customThe organic layer was separated
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe crude residue was purified by silica gel chromatography
- additiona 95:5 mixture of dichloromethane and methanol as eluent
Sources & evidence
- ORD record
- ord-83c00bd9113940e4a8e7718e41f78588
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680139B2
Reaction notes
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