Acetic Acid → HCID 19363420, compound
Reaction equation
CO[C:3]1([C:18]([OH:20])=O)[C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:10][CH:9]=[CH:8][CH:4]1[C:5]([OH:7])=O.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][NH2:30])=[CH:24][CH:23]=1.[C:31](O)(=[O:33])C>>[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][N:30]2[C:18](=[O:20])[C:3]3[C:4](=[CH:8][CH:9]=[C:10]([O:33][CH3:31])[C:11]=3[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:5]2=[O:7])=[CH:24][CH:23]=1Participants
Procedure
2-Methoxy-3-pentyloxyphthalic acid (155 mg, 0.55 mmol, 1 eq) and 2-(4-hydroxyphenyl)ethylamine (101.6 mg, 0.74 mmol, 1.4 eq) were dissolved in acetic acid (10 ml), and the solution was refluxed under heating for 2 hours. The mixture was cooled to room temperature and extracted twice with ethyl acetate (40 ml). The organic layers were combined, washed with a 1N aqueous hydrochloric acid solution (40 ml) and further with saturated brine (40 ml), and dried over anhydrous sodium sulfate. The drying agent was Eltered off, and the filtrate was concentrated under reduced pressure and purified by column chromatography on silica gel (n-hexane/ethyl acetate=4/1) to give 2-[2-(4-hydroxyphenyl)ethyl]-5-methoxy-4-pentyloxyisoindole-1,3-dione (67 mg, 31.8%).
Workup
- temperaturethe solution was refluxed
- temperatureunder heating for 2 hours
- extractionextracted twice with ethyl acetate (40 ml)
- washwashed with a 1N aqueous hydrochloric acid solution (40 ml) and further with saturated brine (40 ml)
- dry with materialdried over anhydrous sodium sulfate
- concentrationthe filtrate was concentrated under reduced pressure
- custompurified by column chromatography on silica gel (n-hexane/ethyl acetate=4/1)
Sources & evidence
- ORD record
- ord-7832b71ffcfa465e8be1a1717836886e
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06017919
Reaction notes
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