2-Methoxy-5-nitroaniline → HCID 67303179, compound

Participants

Reaction Steps

Added 2-methoxy-5-nitro phenylamine (8.0 grams, 47.61 mmol) to a round bottomed flask, followed by the addition of 1-boc-4-piperidone (28.42 grams, 142.83 mmol), sodium sulfate (67.6 grams, 476 mmol) and acetic acid (80 mL). The above reaction mass was stirred for 8 hours at ambient temperature. Then added sodium triacetoxyborohydride (30.28 grams, 142.83 mmol) at 20-25° C. in 5 minutes and stirred the reaction mass for further 3 hours. The reaction mass was quenched into water (100 mL) and basified to pH: 9 with 50% aqueous sodium hydroxide solution. The product was extracted with ethyl acetate (4×50 mL). Combined organic layer was washed with brine (100 mL), dried over sodium sulfate and concentrated to obtain oily product. The product was further purified by column chromatography, the eluent being ethyl acetate, n-hexane and triethylamine, to obtain 24.01 grams of pure product.

Provenance & Evidence