3-Chloro-5-methylbenzenamine

3-Chloro-5-methyl-phenylamine. An ethanol solution (75 mL) containing 1-chloro-3-methyl-5-nitro-benzene (5.0 g, 29 mmol) are added with SnClAn ethanol solution (75 mL) containing 1-chloro-3-methyl-5-nitro-benzene (5.0 g, 29 mmol) were mixed with SnCl3-Chloro-5-nitrotoluene (45 g, 0.241 mol) and ethanol (500 ml) were mixed in a 2 litter four-neck flask. The mixture was cooled to about 4 deg C. A solution of tin chloride monohydrate (217.67 g, 0.965 mol) in 200 ml of ethanol was added dropwise to the mixture over 2 hours, while the reaction mixture was maintained at 10 deg C. or lower. Then the reaction product mixture was stirred at room temperature for 2 hours and poured into 2500 ml of iced water. It was neutralized with sodium hydroxide and filtered with a nutsche filled with sellaite. The residue was washed with ethyl acetate. The intended product was obtained with ethyl acetate from the filtrate liquid. Then the extract liquid and the washing liquid were jointed. The mixture was washed with water and then a saturated salt water and dried with magnesium sulfate. Concentrated, it was treated by distillation at a reduced pressure to obtain 28.0 g of a yellow liquid (production yield 80percent). B.p.: 85-92 deg C./0.4 kPa or lower (3 Torr or lower) 1H-NMR, 500 MHz, in CDCl3 (delta) 6.56 (bs, 1H), 6.48 (dd, JI, J2=1.3 Hz, 1H), 6.36 (bs, 1H), 3.64 (bs, 2H), 2.22 (s, 3H)Example LII; 3-chloro-5-methyl-aniline; 2.4 g of 3-chloro-5-nitro-toluene are dissolved in 35 ml of ethanol, combined with 15.8 g tin dichloride-dihydrate and refluxed for 3 hours. The solvent is eliminated in vacuo, the residue is taken up in 4 M sodium hydroxide solution and filtered through kieselguhr. The filter cake is washed thoroughly with ethyl acetate. The aqueous phase is extracted 3 times with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution and dried on magnesium sulphate. The solvent is eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 81 :15 to 70:30). Yield: 1.59 g (80 percent of theory) Mass spectrum (ESI

Molecular Weight:141.60
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:141.0345270
Monoisotopic Mass:141.0345270
Topological Polar Surface Area:26
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes