1,2-Diamino-3-chlorobenzene synthesis
- Product Name:1,2-Diamino-3-chlorobenzene
- CAS Number:21745-41-5
- Molecular formula:C6H7ClN2
- Molecular Weight:142.59
59483-54-4
21745-41-5
Step 1: 3-chloro-2-nitroaniline (5.0 g, 29 mmol), zinc powder (18.9 g, 290 mmol) and ammonium chloride (31.0 g, 579 mmol) were stirred in 100 mL of a 1:1 ethanol-water mixture for 18 hours at room temperature. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to give a brown solid. The solid was transferred to a partition funnel and partitioned with dichloromethane and water. The organic layer was separated, the organic extracts were combined, dried with anhydrous magnesium sulfate, filtered and the solvent was removed in vacuum to give 3-chlorobenzene-1,2-diamine (4.00 g, 97% yield) as a brown solid.
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Yield: 10.43 g (89%)
Reaction Conditions:
in ethanol;water;hydrogen
Steps:
47 3-Chloro-1,2-phenylenediamine
Example 47 3-Chloro-1,2-phenylenediamine 2-Chloro-6-nitroaniline (14.10 g, 81.71 mmol), Raney-nickel (5.02 g of a 50% slurry in water), and ethanol (200 mL) were combined in an autoclave which was pressurized to 15 psig with hydrogen. The resulting mixture was allowed to stir overnight at RT. The mixture was then filtered through a pad of celite, which was subsequently washed with several portions of methanol, and the solvents were removed by rotary evaporation to afford 10.43 g (89%) of a viscous, brown oil, which darkened upon standing. MS (EI): m/z 143.1 (M+H).
References:
Glaxo Wellcome Inc. US6204249, 2001, B1
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