HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Anhydride → N-(5-Chloro-2-methyl-4-nitrophenyl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | 6-Chloro-4-nitro-o-toluidine | HCID 83772 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(5-Chloro-2-methyl-4-nitrophenyl)acetamide | HCID 304738 | — |
Reaction Steps
5-Chloro-2-methyl-4-nitroaniline was treated with acetic anhydride in the presence of 4-dimethylaminopyridine (DMAP) in CH2Cl2 to provide N-(5-chloro-2-methyl-4-nitrophenyl)acetamide, which was reacted with vinyl magnesium bromide at −40° C. to room temperature to give N-(7-chloro-4-methyl-1H-indol-5-yl)acetamide. Deprotection of the acetyl group by heating in an aqueous HCl solution at the reflux temperature provided 5-amino-7-chloro-4-methylindole.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07781591B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-0afb946d7146462898a1d73d08910c82 |
| Source note | uspto-grants-2010_08 |