Pyridine → 4-dodecyloxycarbonyl-N-hydroxyphthalimide
Reaction equation
[CH2:1]([O:13][C:14]([C:16]1[CH:17]=[C:18]2[C:23](=O)[O:22][C:20](=[O:21])[C:19]2=[CH:25][CH:26]=1)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl.[NH2:28][OH:29].N1C=CC=CC=1>O>[CH2:1]([O:13][C:14]([C:16]1[CH:17]=[C:18]2[C:23](=[O:22])[N:28]([OH:29])[C:20](=[O:21])[C:19]2=[CH:25][CH:26]=1)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In a 500-ml flask equipped with a stirrer, a thermometer and a dropping funnel, 100 g (277.43 mmol) of 4-dodecyloxycarbonylphthalic anhydride, 21.21 g (305.17 mmol) of hydroxylamine hydrochloride and 250 g of pyridine were placed and were stirred at room temperature in an atmosphere of nitrogen gas for 30 minutes, followed by stirring at 90° C. for further 3 hours. The resulting reaction mixture was added dropwise to 3000 g of pure water over 30 minutes with stirring and thereby yielded a crystal of 4-dodecyloxycarbonyl-N-hydroxyphthalimide. The mixture was stirred for further 1 hour, the precipitate was separated by filtration and was rinsed with pure water. The resulting solid was stirred and rinsed in a solvent mixture of 640 g of n-hexane and 160 g of ethyl acetate for 3 hours, the resulting slurry was filtrated, was rinsed with n-hexane, was dried at 60° C. under reduced pressure and thereby yielded 90.88 g (242.04 mmol) of target 4-dodecyloxycarbonyl-N-hydroxyphthalimide as a white powder. The yield was 87.2% on the basis of 4-dodecyloxycarbonylphthalic anhydride.
Workup
- customIn a 500-ml flask equipped with a stirrer
- stirringby stirring at 90° C. for further 3 hours
- customThe resulting reaction mixture
- stirringwith stirring
Sources & evidence
- ORD record
- ord-2470230dec804fdd8c4ea3cbfda3454c
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06998491B2
Reaction notes
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