Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trimethylsilyldiazomethane | HCID 167693 | — |
| Reactant | 4-Fluoroanthranilic acid | HCID 2724967 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Methyl 2-amino-4-fluorobenzoate | HCID 14075433 | 95.3% |
Reaction Steps
2-Amino-4-fluorobenzoic acid (10.0 g, 64.5 mmol) was dissolved in methanol (50 mL) and toluene (150 mL). (Trimethylsilyl)diazomethane (2M in diethyl ether, 48.3 mL, 96.7 mmol) was added over 10 minutes at RT. Stirring was continued for 2 h at RT. Water (300 mL) was added to the mixture and the volatiles were removed in vacuo. The remaining aqueous phase was cooled to 0° C. for 30 minutes and the formed precipitate was collected by filtration, washed with water and dried to give pure title compound (10.4 g, 95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08178544B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-80c573e0d42946fba48078105dd6de80 |
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| Source note | uspto-grants-2012_05 |
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