Acetyl chloride → 2-Nitro-5-(3-phenyl-pyrrol-1-yl)-phenylamine

Participants

Reaction Steps

The title compound was prepared from N-(5-amino-2-nitro-phenyl)-acetamide [prepared from commercially available 5-chloro-2-nitroaniline by the following sequence: i.) nucleophilic aromatic substitution with NaN3 in DMSO at 80° C. for 15 h; ii.) acetylation with AcCl in HOAc at 120° C. for 2 h according to Eur. J. Med. Chem. 1988, 23, 553; iii.) Staudinger-reduction with PPh3/H2O in THF at 23° C. for 1 h] and 2,5-dimethoxy-3-phenyl-tetrahydro-furan [CAS-no. 207119-66-2] in HOAc at 60° C. for 2 days according to the general procedure F. Obtained as a brown solid (414 mg). Deacetylation of this material was perfomed by stirring with 25% HCl in THF at 80° C. for 90 min. Obtained as a brown solid (179 mg).

Provenance & Evidence