Methanol → Methyl 2-amino-3,5-dichlorobenzoate
Reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([Cl:12])[CH:9]=[C:10]([Cl:11])[C:2]=1[NH2:1]Participants
Conditions
- Temperature
- 64 °C
Procedure
To a 500 mL round-bottom flask, 0.2 mol of 2-amino-3,5-dichlorobenzoic acid having a structural formula of IV-4, 300 mL of methanol, and 5 mL of concentrated sulfuric acid were added, heated to 64° C. and reacted for 12 hours (into which 3 mL of concentrated sulfuric acid was added twice), after cooling most of the solvent was removed under reduced pressure, and 300 mL of water was added, the pH was adjusted to 9-10 with a saturated sodium hydroxide solution, extracted with 200 mL of ethyl acetate, washed with water for one time, dried over anhydrous sodium sulfate, filtered and the solvent was remove to obtain a crude product, 34.6 grams of 2-amino-3,5-dichlorobenzoic acid methyl ester having a structure as shown by VIII-1 was obtained by column chromatography, and the yield was 78.6%;
Workup
- additionwas added twice),
- temperatureafter cooling most of the solvent
- customwas removed under reduced pressure, and 300 mL of water
- additionwas added
- extractionextracted with 200 mL of ethyl acetate
- washwashed with water for one time
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customthe solvent was remove
Sources & evidence
- ORD record
- ord-215dc61984c343fa8353c7f55196dbf9
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09301529B2
Reaction notes
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