Hydrochloric Acid → HCID 86702686, compound

Participants

Reaction Conditions

Reaction Steps

Palladium on carbon (5 wt. %, wet, contains ˜50% water, 2.4 g, 0.56 mmol, 0.005 eq) is charged into a 300 mL Parr bomb. Then, methyl 5-hydroxy-3-methyl-2-nitrobenzoate (23.2 g, 0.11 mol, 1 eq) and MeOH (80 mL) are charged. The bomb is sealed, and pressurized/vented three times with hydrogen, and pressured with 100 psi hydrogen. The reaction mixture is stirred, until the hydrogen pressure is not dropping. The bomb is opened, and an HPLC sample shows that the reaction is complete. The mixture is diluted with 80 ml of THF and filtered through a Celite pad. The solution is concentrated under vacuum and solvent is switched to EtOAc. To the suspension in EtOAc (150 mL) at 15° C., HCl in dioxane (4M, 36 mL, 0.14 mol, 1.3 eq) is charged at a rate that the internal temperature is below 30° C. The suspension is stirred at 20° C. for 2 hour. The slurry is filtered. The solid is dried under vacuum to provide the desired product, 2-amino-5-hydroxy-3-methylbenzoate hydrochloride (21.5 g, 90% yield).

Provenance & Evidence