i dissolved 0.8g of mixed harmalas hcl with salt contamination in vinegar water, then added ammonia. there was no precipitation. so i added a sodium hydroxide solution and noticed lots of precipitation of a white fluffy precipitate. when i filtered and dried it turned dark tan like the hcl form, and there was a loss of yield. most of the previous salt form was probably salt, but what im curious about is how a white precip turned into a brown powder.

does this commonly happen?