HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 2-Methyl-4-nitrobenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 4-Nitro-o-toluic acid | HCID 74790 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-Methyl-4-nitrobenzamide | HCID 20165120 | — |
Reaction Steps
To 2-methyl-4-nitrobenzoic acid suspended in CH2Cl2 under Ar was added DMF then oxalyl chloride. The reaction was stirred at room temperature 1.5 hours then the solvent was evaporated. The residue was dissolved in THF and ammonia gas was bubbled through the reaction for 15 minutes. The solvent was evaporated and the residue partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The extracts were dried (MgSO4), filtered and evaporated. Column chromatography (SiO2, 0-100% EtOAc/Hex) gave pure 2-methyl-4-nitrobenzamide (E111).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08450344B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-8d1a8ce6106749d28f794f8034f011a7 |
| Source note | uspto-grants-2013_05 |