Dimethylformamide → 2-Amino-4-fluoro-5-iodo-3-methoxy-6-methylbenzoic Acid
Reaction equation
CN(C)C=O.[I:6]N1C(=O)CCC1=O.[NH2:14][C:15]1[C:23]([O:24][CH3:25])=[C:22]([F:26])[CH:21]=[C:20]([CH3:27])[C:16]=1[C:17]([OH:19])=[O:18]>O>[NH2:14][C:15]1[C:23]([O:24][CH3:25])=[C:22]([F:26])[C:21]([I:6])=[C:20]([CH3:27])[C:16]=1[C:17]([OH:19])=[O:18]Participants
Procedure
An N,N-dimethylformamide (14 ml) solution of N-iodosuccinimide (1.89 g, 8.4 mmol) was dropwise added to an N,N-dimethylformamide (14 ml) solution of 2-amino-4-fluoro-3-methoxy-6-methylbenzoic acid (I-29) (1.4 g), followed by stirring at room temperature for 2 hours and a half. Water was added to the reaction liquid, followed by extraction three times with ethyl acetate, the organic layer was washed with aqueous saturated sodium thiosulfate solution and saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane:ethyl acetate (2:1) was concentrated under reduced pressure to obtain the entitled compound (1.77 g, 78%) as a brown solid.
Workup
- extractionfollowed by extraction three times with ethyl acetate
- washthe organic layer was washed with aqueous saturated sodium thiosulfate solution and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationAfter filtration and concentration under reduced pressure
- concentrationthe eluate with n-hexane:ethyl acetate (2:1) was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-fd8d65771e144e8e8d2ef6eda72bd2eb
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737166B2
Reaction notes
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