2-Bromo-5-methylbenzenamine

Brown crystal

Production Reference Example 36 Example 123[0328] (S)-2-(2-(3-ethyl-2, 4-dimethyl- lH-indol- 1 -yl)acetamido)-N-(6-methoxypyridin-3- yl)-N-methyl-3-phenylpropanamideExample 123A. Preparation of 2-bromo-5-methylbenzenamine[0329] To a solution of bromo-4-methyl-2-nitrobenzene (5 g, 23.3 mmol, 1.0 eq) in MeOH, was added Ranney Nickel (2 mL). The mixture was stirred for 15 minutes, and hydrazine hydrate (2.33 g, 46.6 mmol, 2 eq) was added dropwise. The resulting mixture was stirred for 2 hours at room temperature Then the reaction mixture was filtered, the filtrate was concentrated under vacuum. The residue was washed with HStep 1 :4-bromo-3-nitrotoluene 36a (5.0 g, 22.9 mmol) is dissolved in 50 ml_ ethyl acetate and solid tin(ll) chloride dihydrate (20.0 g, 86.9 mmol) is added. The mixture is heated under nitrogen atmosphere at 7O4-bromo-3-nitrotoluene 36a (5.0 g, 22.9 mmol) is dissolved in 50 mL ethyl acetate and solid tin(ll) chloride dihydrate (20.0 g, 86.9 mmol) is added. The mixture is heated under nitrogen atmosphere at 704-bromo-3-nιtrotoluene 36a (5 0 g, 22 9 mmol) is dissolved in ethyl acetate (50 mL) and solid tιn(ll) chloride dihydrate (20 0 g, 86 9 mmol) is added The mixture is heated under nitrogen atmosphere at 704-bromo-3-nitrotoluene 36a (5.0 g, 22.9 mmol) is dissolved in 50 ml. ethyl acetate and solid tin(ll) chloride dihydrate (20.0 g, 86.9 mmol) is added. The mixture is heated under nitrogen atmosphere at 7O2-bromo-5-methylaniline (1): To a solution of l-bromo-4-methyl-2-nitrobenzene (3.0 g, 13.8 mmol) in dioxane/water (1 : 1; 60 mL), zinc dust (9 g, 138.8 mmol) was added followed by the addition of ammonium chloride (7.3 g, 138.8 mmol). The reaction mixture was stirred at room temperature for 3 h. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 2 (2 g, 77percent) as a pale yellow liquid. 1H NMR (400 MHz, DMSO-dAdd iron powder (7.75 g, 138 mmol), concentrated HC1 (1 mL) and water (10 mL) to a solution of commercially available 4- bromo-3-nitrotoluene (10 g, 46 mmol) in methanol (200 mL) at room temperature under nitrogen and heat the mixture at reflux for 168 h. Remove the solvents under reduced pressure, suspend the residue in 0.1 N NAOH (350 mL) and extract with chloroform (3 x 300 mL). Dry the combined organic extracts over MGS04 and remove the solvents under reduced pressure to afford to afford 2-bromo-5- methylphenylamine (Step 1) as an amber oil (5.87 g, 68percent): 1H NMR (CDC13) 5 2.20 (s, 3H), 4.00 (br s, 2H), 6.40 (d, 1H), 6.60 (s, 1H), 7.20 (d, 1H).

Molecular Weight:186.05
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:184.98401
Monoisotopic Mass:184.98401
Topological Polar Surface Area:26
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes