ChemicalBook CAS DataBase List N1-(3-Aminophenyl)acetamide

N1-(3-Aminophenyl)acetamide synthesis

11synthesis methods

Product Name:N1-(3-Aminophenyl)acetamide
CAS Number:102-28-3
Molecular formula:C8H10N2O
Molecular Weight:150.18

122-28-1

102-28-3

m-Nitroacetanilide (1 g, 5.66 mmol) was dissolved in 100 mL of methanol and a catalytic amount of 10% palladium/activated charcoal (~0.015 g) was added. The reaction mixture was cooled via an ice bath and sodium borohydride (1 g, 26.43 mmol) was added in batches. Subsequently, the mixture was stirred vigorously for 1 hour. The reaction process was monitored by thin layer chromatography (TLC) using toluene-acetone (5:2, v/v) as unfolding agent. Upon completion of the reaction, the product was purified by silica gel column chromatography with toluene-acetone (5:2, v/v) as eluent. A white solid product was obtained in 75% yield with a melting point of 86-88 °C. Elemental analysis (C8H10N2O, Mr=150.18) Calculated values: C 63.98%, H 6.71%, N 18.65%; measured values: C 63.76%, H 6.50%, N 18.53%.1H NMR (400 MHz, DMSO-d6) δ: 9.58 (s, 1H, NH), 6.92 (t, 1H, H-2, J = 2.00 Hz), 6.88 (t, 1H, H-4, J = 8.00 Hz), 6.64 (dd, 1H, H-6, J1 = 0.80 Hz, J2 = 8.00 Hz), 6.23 (dd, 1H, H-5, J1 = 1.60 Hz, J2 = 8.00 Hz), 5.00 (bs, 2H, NH2), 1.99 (s, 3H , CH3-CO).13C NMR (100 MHz, DMSO-d6) δ: 167.85 (C=O), 148.85 (C1), 139.85 (C3), 128.75 (C4), 109.04 (C5), 106.93 (C6), 104.67 (C2), 23.98 (CH3-CO).

108-45-2 Synthesis

108-45-2
477 suppliers
$13.00/25g

106-50-3 Synthesis

106-50-3
620 suppliers
$19.00/25g

102-28-3
335 suppliers
$5.00/25g

Yield:102-28-3 88.5%

Steps:

2 EXAMPLE 2
EXAMPLE 2 In place of the 1,4-phenylenediamine (108 parts) used in Example 1 there is used 1,3-phenylenediamine (108 parts). 3-Aminoacetanilide is obtained in 88.5% theory yield.

References:

Imperial Chemical Industries Limited US4079079, 1978, A

122-28-1 Synthesis

122-28-1
124 suppliers
$15.00/5mg

102-28-3
335 suppliers
$5.00/25g

References

108-45-2 Synthesis

108-45-2
477 suppliers
$13.00/25g

64-19-7 Synthesis