Sodium Azide → 2-Nitro-4-chloro-5-allyloxyaniline

Participants

Reaction Steps

The product of step (b) (66.1 g, 267 mmol) was dissolved in 600 ml DMF at ambient temperature. Sodium azide (19.1 g, 267 mmol) was added and the mixture allowed to stir over a 4-day weekend, after which another 2 g (30.8 mmol) of the azide were added. Sodium borohydride (2.77 g, 73.5 mmol) was added in small portions while cooling in an ice bath. The mixture was stirred over night and then another 0.85 g (0.015 m) of sodium borohydride were added portionwise to the cold mixture. When the reaction appeared complete, the mixture was poured over ice water, the product filtered and dried to yield 50.5 g of 2-nitro-4-chloro-5-allyloxyaniline.

Provenance & Evidence