3,4-Dichloro-1,2-benzenediamine synthesis

6synthesis methods

Product Name:3,4-Dichloro-1,2-benzenediamine
CAS Number:1668-01-5
Molecular formula:C6H6Cl2N2
Molecular Weight:177.03

65078-77-5 Synthesis

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Yield:1668-01-5 94%

Reaction Conditions:

with hydrogenchloride;dichloro-λ²-stannane dihydrate in methanol;lithium hydroxide monohydrate at 70; for 4 h;

Steps:

Intermediate 25 3,4-dichlorobenzene-1,2-diamine

Intermediate 25 3.4- dichlorobenzene-l ^-diamine To a solution of 2,3-dichloro-6-nitroaniline, available via a literature method (Carta et al., 2007) (1.08 g, 5.21 mmol) in MeOH (4.40 mL) was added a solution of tin(II)chloride dihydrate (4.71 g, 20.87 mmol) in concentrated HC1 (6.60 mL). The reaction was heated at 70°C for 4 h. The reaction mixture was concentrated to half the volume, basified with 5M NaOH(aq), diluted with EtOAc (20 mL) and stirred for 30 min. The resulting precipitate was removed by filtration. The filtrate was washed with brine (20 mL), dried (Na₂SC>4), filtered and concentrated to give the desired product as a pale brown solid (0.87 g, 94%); m/z = 176.9, 178.9 (MH)⁺.

References:

WO2015/177367,2015,A1 Location in patent:Page/Page column 70