Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Potassium Bicarbonate | HCID 516893 | — |
| Reactant | HCID 58964477 | HCID 58964477 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58964475 | HCID 58964475 | 79.1% |
Reaction Steps
0.12 ml of sulfuric acid 98% are added dropwise at 0° C. (exothermic) to a suspension of 69 mg (0.257 mmol) of 2-acetylamino-5-methoxy-4-nitro-benzoic acid methyl ester, 0.69 ml of methanol and 0.12 ml of water. The mixture is then heated to 70° C. for 30 minutes, cooled to room temperature, poured onto a mixture of ice, water and ethyl acetate and the pH adjusted to 6 with concentrated potassium bicarbonate solution. The organic phase is separated, washed with brine, dried over sodium sulfate, filtered and evaporated, giving 46 mg (79%) of 2-amino-5-methoxy-4-nitro-benzoic acid methyl ester as red-brown crystals, m.p. 127-129° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08299085B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-078548694d594bfca9eb8158254a1b3b |
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| Source note | uspto-grants-2012_10 |
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