Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | Methyl 4-chloro-3-methoxy-5-nitrobenzoate | HCID 49757533 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86340167 | HCID 86340167 | 100% |
Reaction Steps
Methyl 4-chloro-3-methoxy-5-nitrobenzoate (available from, for example, Apollo Scientific Ltd) (14 g, 57.0 mmol) was dissolved in N,N-dimethylformamide (DMF) (140 mL) and cooled to ˜0° C. in an ice/water bath. Methanamine (2M in THF) (114 mL, 228 mmol) was added dropwise with vigorous stirring using a dropping funnel and the mixture was flushed with nitrogen and heated at 80° C. for 3 hr. The mixture was allowed to cool to room temperature over the weekend. The reaction mixture was diluted with water (500 mL), and filtered under vacuum to give the title compound as an orange solid (13.69 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09127003B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-2a29b6b84f7446af8cf239e56ed68698 |
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| Source note | uspto-grants-2015_09 |
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