Sodium Carbonate → 2-(Chloromethyl)quinoline
Reaction equation
[Cl:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>>[Cl:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1Participants
Procedure
Monomer IV can be obtained by following this general procedure: A mixture of 2-(chloromethyl)quinoline·HCl and a 1% sodium carbonate solution is added to a separatory funnel, and extracted with methylene chloride. The methylene chloride extracts are passed through a cone of anhydrous sodium sulfate, and collected in a flask. 2-(Chloromethyl)quinoline is obtained in the flask after evaporation of the methylene chloride. To the flask containing 2-(chloromethyl)quinoline, is added MEHQ and acetone. The mixture is heated to about 56° C. DMAPMA is added to the solution. The resulting mixture is heated for about 110 min at 56° C., then cooled to about 25° C. for 2 hrs. The resulting white solid, the quaternary ammonium salt of DMAPMA and 2-(chloromethyl)quinoline is isolated by filtration.
Workup
- extractionextracted with methylene chloride
- customcollected in a flask
Sources & evidence
- ORD record
- ord-395ac1ceed824613aadf8ba169945f54
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06380431B1
Reaction notes
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