3,5-Dichloro-4-methylaniline

Preparation 1; 3 , 5 -dichloro-4-methylaniline; Dissolve 1, 3 -dichloro-2-methyl-5 -nitrobenzene (0.50 g, 2.43 mmol) in DMF and treat with tin (II) chloride dihydrate (2.74 g, 12.1 mmol) in a single portion. Stir the reaction for 1 hour and dilute with ethyl acetate and filter through celite. Wash the filtrate four times with water and twice with brine, dry over MgSOPreparation 8; 3 , 5 -dichloro-4-methylaniline; Dissolve l, 3-dichloro-2-methyl-5-nitrobenzene (0.50 g, 2.43 mmol) in DMF and treat with tin (II) chloride dihydrate (2.74 g, 12.1 mmol) in a single portion. Stir the reaction for 1 hour, dilute with ethyl acetate, and filter through celite. Wash the filtrate four times with water and twice with brine, dry over MgSOPurged a 50-mL round-bottomed flask with argon. Charged l, 3-dichloro-2-methyl-5- nitrobenzene (500 mg, 2.43 mmol, Eq: 1.00; from Maybridge), iron (678 mg, 12.1 mmol, Eq: 5.0), ammonium chloride (1.3 g, 24.3 mmol, Eq: 10.0), methanol (10 mL), and water (5 mL) while purging with argon. Fitted the reaction flask with a condenser, then sealed under a positive pressure of argon. Heated at reflux for 2 h, then cooled to room temperature. Stirred over weekend at room temperature. HPLC showed the reaction was complete. Filtered the reaction mixture through a bed of celite, rinsing with methanol. Concentrated filtrate. Added water and ethyl acetate, then added solid sodium bicarbonate. Transferred the mixture to a separatory funnel and added more ethyl acetate. Split layers and washed the organic layer with saturated sodium chloride solution. Dried over magnesium sulfate, filtered, and concentrated. Obtained 0.28 g (65.5percent) of 3, 5-dichloro-4-methylaniline as a yellow solid. The

Molecular Weight:176.04
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:174.9955546
Monoisotopic Mass:174.9955546
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:106
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes