Potassium Hydroxide → HCID 22904614, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-:13].[K+].[CH:15]([O:18][C:19](=[O:22])[CH2:20]Br)([CH3:17])[CH3:16]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH3:16][CH:15]([O:18][C:19]([CH2:20][N:1]([CH2:20][C:19]([O:18][CH:15]([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:3]=[C:4]([CH:8]2[O:9][CH2:10][CH2:11][O:12]2)[CH:5]=[CH:6][CH:7]=1)=[O:22])[CH3:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
165.19 g (1.00 mol) of 2-(3-aminophenyl)-1,3-dioxolan (CA 108 (15): 131815 r), 156.35 g (3.00 mol) of pulverized potassium hydroxide and 11.39 g (0.05 mol) of benzyltriethylammonium chloride are vigorously mechanically stirred under argon and heated to 80° C. 543.09 g (3.00 mol) of bromoacetic acid isopropyl ester is instilled in the suspension and the reaction mixture is stirred for about 8 hours at 80° C. Then, it is filtered, the filtrate is shaken out several times with concentrated aqueous sodium bicarbonate solution, the organic phase is dried on anhydrous magnesium sulfate, filtered and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel 60 (Merck) with methylene chloride/methanol. After concentration by evaporation, the product fractions yield a colorless oil.
Workup
- filtrationThen, it is filtered
- stirringthe filtrate is shaken out several times with concentrated aqueous sodium bicarbonate solution
- dry with materialthe organic phase is dried on anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated by evaporation in a vacuum
- customThe residue is chromatographed on silica gel 60 (Merck) with methylene chloride/methanol
- concentrationAfter concentration
- customby evaporation
- customthe product fractions yield a colorless oil
Sources & evidence
- ORD record
- ord-414ae294111346948c54c9e7c768afca
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05674467
Reaction notes
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