4-Amino-3,5-dimethylphenol

Brown Solid

4-hydroxy-2,6-dimethylaniline is a substituted aniline in which the aniline ring carries 4-hydroxy and 2,6-dimethyl substituents; a urinary metabolite of lidocaine. It has a role as a drug metabolite. It is a substituted aniline and a member of phenols.

An aqueous solution (4 ml) of sodium nitrite (1.90 g, 27.5 mmol) was added to an aqueous solution (20 ml) of sodium sulfanilate dihydrate (5.78 g, 25.0 mmol). The resulting solution was dropped into a beaker containing concentrated hydrochloric acid (5.1 ml) and ice (30 g), and the resulting mixture was kept cold in an ice bath for 20 minutes to prepare solution A. An aqueous solution (30 ml) of sodium hydroxide (5.50 g, 138 mmol) and ice (20 g) were added to 3, 5-dimethylphenol (3.05 g, 250 mmol) to effect dissolution, and then solution A was added dropwise thereto in an ice bath. The resulting solution was stirred in the ice bath for 1 hour and then heated to 65°C to 75°C, and sodium dithionate (16.8 g, 96.5 mmol) was added thereto until the solution lost its color. The solution was cooled to room temperature and stirred for 30 minutes, and the solid formed was collected by filtration and dried to obtain 4-amino-3, 5-dimethylphenol (2.46 g, 72percent).General procedure: A mixture of the para-benzoquinone mono-oxime (1.26 mmol), SnCl2 (0.72 g, 3.80 mmol), 20 mL of CH2Cl2, and 0.2 mL of concentrated HCl, was heated to reflux for 16 h. The CH2Cl2 was removed under reduced pressure, and the residue was dissolved in ethyl acetate and washed with concentrated aqueous NaHCO3. The organic layer was dried over anhydrous Na2SO4 and the filtrate was concentrated under reduced pressure to afford the solid product.

A major Lidocaine metabolite.

Molecular Weight:137.18
XLogP3:0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:137.084063974
Monoisotopic Mass:137.084063974
Topological Polar Surface Area:46.2
Heavy Atom Count:10
Complexity:104
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes