Hydrochloric Acid → HCID 135993593, compound

Participants

Reaction Conditions

Reaction Steps

In a 1000 ml 3-neck round bottom flask equipped with a magnetic stirrer was added 5-chloro-2-nitroaniline (Acros Organics, 29.9 g, 173 mmol), concentrated aqueous HCl (36.5-38.0%, 75 ml), 150 ml deionized water, and 150 ml absolute ethanol. The suspension was cooled to −10° C. and a solution of sodium nitrite (Sigma-Aldrich, 12.7 g, 184 mmol) in 50 ml water was added dropwise over 30 minutes at −10° C. The reaction mixture was stirred for 1 hour and 324 mg sulfamic acid (Aldrich) was added. After 10 minutes of stirring the solids were filtered out and the cold solution was set aside. A NaOH solution was prepared by dissolving NaOH (Aldrich, 37.7 g, 944 mmol) in 120 ml deionized water. Approximately one fourth of the sodium hydroxide solution was added dropwise to a solution of 4-allyl-2-(hydroxymethyl)-6-methoxyphenol from Example 1 in 100 ml water and 300 ml absolute ethanol. The diazonium mixture and remaining NaOH solution were concurrently added dropwise over 1 hr to the 4-allyl-2-(hydroxymethyl)-6-methoxyphenol solution at −10° C. The resulting dark mixture was stirred at 0° C. for 1 hour and ambient temperature for 2 hours. The contents were poured into 3 liters deionized water and the pH was adjusted to 5 using 1 N HCl. The solid was filtered and dried at 50° C. for 64 hours using P2O5 drying agent to afford 28 g (46%) that was used in the next step without further purification.

Provenance & Evidence