HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methyl-3-nitroaniline → N-(4-methyl-3-nitrophenyl)cyclopropanecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methyl-3-nitroaniline | HCID 8390 | — |
| Reactant | Cyclopropanecarboxylic acid | HCID 15655 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | N-(4-methyl-3-nitrophenyl)cyclopropanecarboxamide | HCID 4104437 | 93.9% |
Reaction Steps
To a solution of (4-methyl-3-nitrophenyl)amine (304 mg) in DMF (3 mL) were added cyclopropanecarboxylic acid (258 mg), HATU (1.14 g) and iPr2NEt (1.55 g) successively, and the mixture was stirred at room temperature for 16 hr under a nitrogen atmosphere. The reaction mixture was diluted with EtOAc (15 mL) and the resulted mixture was washed with 1 M HCl (15 mL×2), saturated aqueous NaHCO3 (15 mL×2) and brine, dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with EtOAc-hexane (1:2) to give N-(4-methyl-3-nitrophenyl)cyclopropanecarboxamide (413 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173684B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-bca658655c604b3d9c42e3007194f17b |
| Source note | uspto-grants-2012_05 |