Potassium Carbonate → Ethyl 6-iodo-1-(2-morpholinoethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
Reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH2:9])[CH2:3][CH2:2]1.CN(C)/[CH:12]=[C:13](/[C:19](=[O:28])[C:20]1[CH:25]=[C:24]([I:26])[CH:23]=[CH:22][C:21]=1F)\[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>>[I:26][C:24]1[CH:25]=[C:20]2[C:21](=[CH:22][CH:23]=1)[N:9]([CH2:8][CH2:7][N:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:19]2=[O:28]Participants
4
Conditions
- Temperature
- 40 °C
Procedure
2-Morpholinoethanamine (0.88 g, 6.7 mmol) was added to the stock solution of (Z)-ethyl 3-(dimethylamino)-2-(3-iodobenzoyl)acrylate (Intermediate 24, 0.38M, 18 mL, 7 mmol) and the mixture was heated at 40° C. for 3 h. The solvent was removed in vacuo and the resulting residue was dried in a vacuum oven for 1.5 h. The residue was then dissolved in dimethyl formamide (5 mL) and potassium carbonate powder (1.2 g, 10 mmol) was added. The reaction was heated at 70° C. for a further 3 h then cooled to room temperature. The crude reaction mixture was placed into a fridge for a 3 h. The solid precipitate that formed was collected by filtration, washed with a small amount of dimethylformamide, followed by water, then dried under high vacuum.
Workup
- customThe solvent was removed in vacuo
- customthe resulting residue was dried in a vacuum oven for 1.5 h
- dissolutionThe residue was then dissolved in dimethyl formamide (5 mL)
- temperatureThe reaction was heated at 70° C. for a further 3 h
- temperaturethen cooled to room temperature
- customThe crude reaction mixture
- customThe solid precipitate that formed
- filtrationwas collected by filtration
- washwashed with a small amount of dimethylformamide
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-09b3707fcd324b05b3d0596494c6d70b
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283361B2
Reaction notes
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