3-(3-aminophenyl)-N-methylpropanamide(SALTDATA: 2HCl) synthesis

Yield: 2.5 g

Reaction Conditions:

with triethylsilane;palladium on activated charcoal in methanol at 20; for 1 h;

Steps:

ix.b Step b: Synthesis of 3-(3-aminophenyl)- methyl propanamide
To a stirred solution of N-methyl-3-(3-nitrophenyl)acrylamide (4 g, 19.40 mmol) and Pd-C ( 10%, 200 mg) in MeOH (30.0 ml) was added triethylsilane (31 ml, 194 mmol) dropwise at room temperature over a period of lhr. Reaction progress was monitored by TLC. After completion of reaction, reaction mixture was filtered through celite bed. The filtrate was concentrated under vacuum to give the title compound (2.5 gm). ⁱHNMR (400 MHz, DMSO-d6), δ 7.76-7.75 (d, lH,J=4Hz), 6.96-6.88 (m, lH), 6.38- 6.32 (m,3H), 5. 10 (s,2H), 2.62-2.58 (t,2H J=6.8Hz), 2.55-2.54 (d,3H J=4.4Hz) 2.32- 2.25 (t,2H J=6.9Hz). GCMS: 177.88 [M+] .

References:

LUPIN LIMITED;DAVE, Bhavesh;BANERJEE, Rakesh, Kumar;PHUKAN, Samiron;KHOJE, Abhijit, Datta;HANGARGE, Rajkumar;JADHAV, Jitendra, Sambhaji;PALLE, Venkata, P.;KAMBOJ, Rajender, Kumar WO2013/136249, 2013, A1 Location in patent:Page/Page column 53