Acetyl chloride → HCID 18659970, compound
Reaction equation
C(N(C(C)C)CC)(C)C.[C:10](Cl)(=[O:12])[CH3:11].[OH:14][CH:15]1[C:24]2[N:23]=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH2:18][CH:17]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[CH2:16]1>CN(C)C1C=CN=CC=1.ClCCl>[C:10]([O:14][C@@H:15]1[C:24]2[N:23]=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH2:18][C@H:17]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[CH2:16]1)(=[O:12])[CH3:11]Participants
Procedure
Diisopropylethylamine (0.51 g, 3.9 mmol), a catalytic amount of 4-dimethylaminopyridine and a solution of acetyl chloride (0.31 g, 3.9 mmol) in dichloromethane (5 ml) were added slowly to a solution of 5,6,7, 8-tetrahydro-8-hydroxy-6-((4-methoxyphenyl)methyl)-3-methylquinoline (1.12 g, 3.9 mmol) in dichloromethane (7 ml) at room temperature. The mixture was stirred overnight before further additions of acetyl chloride (0.32 g, 4 mmol) and diisopropylethylamine (0.51 g, 4 mnmol) were made. The mixture was again stirred overnight then diluted with dichloromethane (15 ml) and washed with water (1×15 ml), sodium hydrogen carbonate (1×15 ml), brine (1×15 ml) and water (1×15 ml). After drying (MgSO4) the reaction mixture was concentrated under reduced pressure to give an oil (1.46 g). This product was chromatographed on silica gel eluting with ethyl acetate/hexane (1:1) to give a fraction which on evaporation gave a solid (0.8 g). The solid was recrystallised from hexane to afford the title compound, (0.45 g), mp 113°-115° C., [α]D27 =+46° (1%CHCl3).
Workup
- washwashed with water (1×15 ml), sodium hydrogen carbonate (1×15 ml), brine (1×15 ml) and water (1×15 ml)
- dry with materialAfter drying (MgSO4) the reaction mixture
- concentrationwas concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5fb4159f9f2d402994e0a600aadb862e
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05753676
Reaction notes
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