Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Benzoic acid, 5-methoxy-2-methyl-3-nitro-, methyl ester | HCID 53399479 | — |
| Catalyst | Iron | HCID 23925 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 84665992 | HCID 84665992 | 80.9% |
Reaction Steps
To a stirred solution of methyl 5-methoxy-2-methyl-3-nitrobenzoate (1.7 g, 7.6 mmol) in ethanol (20 mL) was added ammonium chloride (1.7 g, 32 mmol) dissolved in water (20 mL) and iron powder (3.38 g, 60.44 mmol). The mixture was heated at 80° C. for 3 h, filtered and the residue washed well with hot ethanol. The filtrate was concentrated and the residue was basified with aqueous sodium bicarbonate. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with water, dried, and concentrated under reduced pressure to give the crude title compound (1.2 g) which was used directly in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09376422B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-4eeb3cc9326e4c23b233baf73eaf3899 |
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| Source note | uspto-grants-2016_06 |
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