1-Chloro-2,4-Dinitrobenzene → HCID 20267379, compound

Participants

Reaction Steps

The dark butanolic solution, obtained according to European Pat. No. 0,011,048 by reaction of 213 parts of 2,4-dinitrochlorobenzene with 632 parts of n-butanol and 42 parts of sodium hydroxide, after hydrogenation and acetylation, of 6-n-butoxy-3-acetylamino-aniline which, according to HPLC analysis, contains, in addition to 195 parts of target product, 11.9 parts of 2,4-bis-acetylamino-1-n-butoxy-benzene and 8.1 parts of 2,4-diamino-1-n-butoxybenzene, in addition to unknown decomposition products formed by oxidation, is precipitated by gassing with 35-40 parts of hydrogen chloride at 20°-30° C. for one hour and, after cooling to 0°-5° C., the precipitate is filtered off with suction, washed twice with 50 parts of methanol each time and dried in vacuo. 221.2 parts of 6-n-butoxy-3-acetylamino-aniline hydrochloride are obtained which, besides about 3% of magnesium chloride, contains no impurities at all which can be detected by HPLC analysis (purity by diazotization: 95.8%). This corresponds to a yield of 214.1 parts of 100% pure 6-n-butoxy-3-acetylamino-aniline hydrochloride (82.8% of theory, based on 2,4-dinitrochlorobenzene).

Provenance & Evidence