ChemicalBook CAS DataBase List 4-(N-Methylamino)benzonitrile

4-(N-Methylamino)benzonitrile synthesis

15synthesis methods

Product Name:4-(N-Methylamino)benzonitrile
CAS Number:4714-62-9
Molecular formula:C8H8N2
Molecular Weight:132.16

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Yield: 52%

Reaction Conditions:

with potassium carbonate;dimethyl sulfate in water;acetone

Steps:

8 4-N-Methylaminobenzonitrile
4-N-Methylaminobenzonitrile A mixture of 4-aminobenzonitrile (2 g, 17 mmol), dimethyl sulfate (1.66 mL, 17 mmol), potassium carbonate (5 g, 35.7 mmol) and acetone (30 mL) was refluxed for 19 hrs. The acetone was removed and water added. The solution was extracted with dichloromethane and upon drying and solvent removal the crude material was subject to column chromatography (silica, ethyl acetate/pentane, 2.5:7.5, Rf 0.37). Recrystallisation from dichloromethane/pentane gave the title compound as a white crystalline solid (1.16 g, 52%) m.p. 88-91° C. ¹H n.m.r. [400 MHZ, CDCl₃] δ 7.43, d, J 8.8 Hz, 2H, H2,6; 6.55, d, J 8.8 Hz, 2H, H3,5; 4.27, br s, 1H, NH; 2.93, s, 3H, NCH₃. ¹³C n.m.r. [100 MHZ, CDCl₃] δ 152.2, C4; 133.52, C2,6; 120.58, CN; 111.70, C3,5; 98.09, C1; 29.82, CH₃.

References:

Peter MacCallum Cancer Institute US6548505, 2003, B1

67-56-1 Synthesis