Acetyl chloride → 4-Iodo-2-nitro-5-pyrrol-1-yl-phenylamine

Participants

Reaction Steps

The title compound was prepared from N-(5-amino-4-iodo-2-nitro-phenyl)-acetamide (228 mg, 0.71 mmol) [prepared from commercially available 5-chloro-2-nitroaniline by the following sequence: i.) iodination with iodine monochloride, NaOAc in HOAc according to Wilson, J. Gerald; Hunt, Frederick C. Aust. J. Chem. 1983, 36, 2317-25; ii.) nucleophilic aromatic substitution with NaN3 in DMSO at 80° C. for 15 h; iii.) acetylation with AcCl in HOAc at 120° C. for 2 h according to Eur. J. Med. Chem. 1988, 23, 553; iv.) Staudinger-reduction with PPh3/H2O in THF at 23° C. for 1 h] and 2,5-dimethoxytetrahydrofuran (0.14 mL, 1.08 mmol) in HOAc (10 mL) at 95° C. for 2 h according to the general procedure F. Obtained as a yellow solid (221 mg). Deacetylation of this material (371 mg, 1.0 mmol) was perfomed by stirring with 1 N NaOH (2.0 mL, 2.0 mmol) in THF (3.4 mL) at 60° C. for 21 h. Obtained as a yellow solid (312 mg).

Provenance & Evidence