Methanol → Methyl 5-Amino-2-chlorobenzoate
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([NH2:11])[CH:9]=[CH:10][C:2]=1[Cl:1]Participants
4
Conditions
- Temperature
- 86 °C
Procedure
2-Chloro-5-aminobenzoic acid (1.5 g, 8.74 mmol) was dissolved in methanol (8 ml) and sulphuric acid (1 ml) was added drop wise with stirring. The reaction mixture was then heated to 86° C. for 18 hr then allowed to cool to room temperature before solvent was removed in vacuo. The resultant purple solid was then dissolved in water and 5M NaOH solution was added until pH 7 was reached. This was then washed with ethyl acetate. The organics were dried over Na2SO4 and solvent was removed in vacuo to give the title compound as a purple oil (1.51 g, 8.12 mmol, 93%): LCMS: [M+H]+=186, Rt=0.88 min, 95% purity.
Workup
- temperatureto cool to room temperature before solvent
- customwas removed in vacuo
- dissolutionThe resultant purple solid was then dissolved in water
- addition5M NaOH solution was added until pH 7
- washThis was then washed with ethyl acetate
- dry with materialThe organics were dried over Na2SO4 and solvent
- customwas removed in vacuo
Sources & evidence
- ORD record
- ord-0d351c17f26a4bff9c6d277a6f2f8bf8
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071607B2
Reaction notes
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