ChemicalBook CAS DataBase List 2-Amino-5-Methyl-Benzonitrile

2-Amino-5-Methyl-Benzonitrile synthesis

13synthesis methods

Product Name:2-Amino-5-Methyl-Benzonitrile
CAS Number:5925-93-9
Molecular formula:C8H8N2
Molecular Weight:132.16

64113-86-6 Synthesis

64113-86-6
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5925-93-9
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Yield: 99%

Reaction Conditions:

Stage #1:2-nitro-5-methylbenzonitrile with hydrogenchloride;tin(ll) chloride in ethanol;water at 20 - 30; for 1 h;
Stage #2: with sodium hydroxide in ethanol;water; pH=7

Steps:

14.b
5-Methyl-2-nitrobenzonitrile (1.92 g, 11.84 mmol) was added in portions to a stirred solution of SnCl₂ (11.22 g, 59.2 mmol) in conc. HCl (12 mL) and EtOH (12 mL). The reaction temperature was maintained at 20-30° C. using an ice bath. The reaction mixture was then stirred at room temperature for 1 h and poured into an ice cold aqueous solution of NaOH (6N, app. 30 mL) to neutralize to pH7. The product was extracted into EtOAc, washed with brine, dried over MgSO₄ and concentrated to provide the title product (1.56 g, 99%) as a yellow-brown solid. ¹H NMR (400 MHz, DMSO-d₆) δ 2.21 (s, 3H), 5.79 (bs, 2H), 6.68-6.71 (d, 1H), 7.10-7.13 (dd, 1H), 7.15 (s, 1H). ¹³C NMR (DMSO-d₆) δ 20.13, 93.99, 116.12, 118.94, 125.38, 132.32, 135.76, 150.21. MS 133 (MH⁺).

References:

SENOMYX, INC. US2008/306053, 2008, A1 Location in patent:Page/Page column 60

29289-13-2 Synthesis