3-Chloro-N,2-dimethylaniline synthesis

5synthesis methods

Product Name:3-Chloro-N,2-dimethylaniline
CAS Number:41456-52-4
Molecular formula:C8H10ClN
Molecular Weight:155.62

71862-02-7 Synthesis

71862-02-7
20 suppliers
$28.60/250mg

41456-52-4
25 suppliers
$105.00/1g

Yield:41456-52-4 79%

Reaction Conditions:

Stage #1: N-(3-chloro-2-methylphenyl)formamidewith borane-THF in tetrahydrofuran at -40 - 20;
Stage #2: with hydrogenchloride;water in tetrahydrofuran at 20;
Stage #3: with sodium hydroxide in water;acetonitrile;

Steps:

11.b

(b) (3-Chloro-2-methylphenyl)methanamine; Borane-tetrahydrofuran (1 M in THF, 61 mL, 61 mmol) was added dropwise to λ/-(3-chloro-2-methylphenyl)formamide (3.43 g, 20.2 mmol; see step (a) above) in THF (25 mL) at -40 ⁰C. The mixture was allowed to warm to rt and HCI (aq, 0.1 M) was added. The mixture was extracted with MeOfBu and the combined extracts were washed with water and brine, dried over Na₂SO₄ and concentrated. The residue was dissolved in Et₂O (30 mL) and HCI (4 M in dioxane, 5.5 mL) was added. The precipitate was collected and dissolved in acetonitrile (5 mL). NaOH (aq, 2 M, 15 mL) was added and the mixture was extracted with MeOfBu. The combined extracts were washed with water, brine and dried over Na₂SO₄. Concentration and vacuum distillation afforded the sub-title compound (2.5 g, 79% yield) as a colourless oil.

References:

WO2008/129288,2008,A2 Location in patent:Page/Page column 57