Dimethylformamide → Methyl 5-chloro-2-methyl-3-nitrobenzoate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:15]N(C=O)C.IC.C(=O)([O-])[O-].[Na+].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:15])=[O:8]Participants
5
Conditions
- Temperature
- 60 °C
Procedure
To a stirred solution of 5-chloro-2-methyl-3-nitrobenzoic acid (1 equiv.) in DMF (3 ml per 1 mmol), iodomethane (4 equiv.) and sodium carbonate (4 equiv.) were added. The resulting reaction mixture was stirred at 60° C. for 8 h. On completion, the reaction mixture was filtered and the inorganic solid residue washed with ethyl acetate. The combined filtrate was concentrated under vacuum till dryness. The residue was re-dissolved in ethyl acetate and washed with 5% sodium bicarbonate solution followed by 5M HCl solution. Organic layer was finally washed with brine, dried over sodium sulfate and concentrated to afford pure methyl 5-chloro-2-methyl-3-nitrobenzoate (90-95%).
Workup
- customThe resulting reaction mixture
- filtrationOn completion, the reaction mixture was filtered
- washthe inorganic solid residue washed with ethyl acetate
- concentrationThe combined filtrate was concentrated under vacuum till dryness
- dissolutionThe residue was re-dissolved in ethyl acetate
- washwashed with 5% sodium bicarbonate solution
- washOrganic layer was finally washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-60bb09446a2f4115b0b97a41d8b0cd03
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598167B1
Reaction notes
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