3-(4-Nitrophenyl)propionic acid

Yellow to brown solidChEBI: A monocarboxylic acid that is 3-phenylpropionic acid in which the hydrogen at the para position of the phennyl group has been replaced by a nitro group.

3-(p-nitrophenyl)propanoic acid is a monocarboxylic acid that is 3-phenylpropionic acid in which the hydrogen at the para position of the phennyl group has been replaced by a nitro group. It has a role as a chromogenic compound. It is a monocarboxylic acid and a C-nitro compound. It derives from a 3-phenylpropionic acid.

Preparation of 4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine; [Show Image] Step 1: Preparation of 3-(4-nitro-phenyl)-propionic acid; To a 1000 ml three-necked flask equippeded with a thermometer were added 50.0 g (332.9 mmol) 3-phenylpropionic acid, 225 ml glacial acetic acid and 125 ml concentrated sulfuric acid, and added dropwise an acid mixture of 25.7 ml 65% nitric acid (366.2 mmol) and 35 ml concentrated sulfuric acid, premixed and cooled to about 5C. The mixture was placed in ice-bath to keep the inside temperature at 18-25C, maintained at 20-25C and stirred for 5 hours. The reaction was poured into 500 g ice, the precipitated solid was filtered, washed with water until neutrality, dried and recrystallized with ethanol to obtain a 35.8 g product as a white solid in a yield of 55.1%, 166-167 .1H-NMR(CDCl3, 400 MHz) delta: 2.62(2H, t, J=7.56Hz), 2.96(2H, t, J=7.56Hz), 7.53(2H, d, J=8.68Hz, ArH), 8.15(2H, d, J=8.68Hz, ArH), 12.22(1H, s, COOH); ESI-MS m/e (%): 218.0(M+Na, 27), 213.4(M+NH3, 3), 196.1(M+1, 100).Preparation of 4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine; Step 1: Preparation of 3-(4-nitro-phenyl)-propionic acid; To a 1000 ml three-necked flask equipped with a thermometer were added 50.0 g (332.9 mmol) 3-phenylpropionic acid, 225 ml glacial acetic acid and 125 ml concentrated sulfuric acid, and added dropwise an acid mixture of 25.7 ml 65% nitric acid (366.2 mmol) and 35 ml concentrated sulfuric acid, premixed and cooled to about 5 C. The mixture was placed in ice-bath to keep the inside temperature at 18-25 C., maintained at 20-25 C. and stirred for 5 hours. The reaction was poured into 500 g ice, the precipitated solid was filtered, washed with water until neutrality, dried and recrystallized with ethanol to obtain a 35.8 g product as a white solid in a yield of 55.1%, 166-167 . 1H-NMR (CDCl3, 400 MHz) delta: 2.62 (2H, t, J=7.56 Hz), 2.96 (2H, t, J=7.56 Hz), 7.53 (2H, d, J=8.68 Hz, ArH), 8.15 (2H, d, J=8.68 Hz, ArH), 12.22 (1H, s, COOH); ESI-MS m/e (%): 218.0 (M+Na, 27), 213.4 (M+NH3, 3), 196.1 (M+1, 100).To a mixture of concentrated nitric acid (1.5 mL, 21.98 mmol) in concentrated sulfuric acid (20 mL) was added phenylpropionic acid (3 g, 19.98 mmol) in portions while maintaining the internal temperature below 0 C. After 1h, the resulting mixture was pour into 20 mL ice water and filtered, the solids were washed with water (5 ml × 2). The filter cake was dried in vacuum to afford product 2a (1.3 g, 33.3%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta: 12.53 (s, 1H, COOH), 8.14 (d, J = 8.61 Hz, 2H, ArH), 7.52 (d, J = 8.61 Hz, 2H, ArH), 2.95 (t, J = 7.45 Hz, 2H, COCH2), 2.83 (t, J = 7.45 Hz, 2H, ArCH2).p-nitrohydrocinnamic acid STR21 In a 2-liter, 3-necked, round-bottomed flask equipped with mechanical stirrer, thermometer, and additional funnel was placed 361 g (2.41 mol) of hydrocinnamic acid which was warmed to 50 to maintain it in a liquid state. To the warm liquid was added slowly dropwise over a 4 hour period with good stirring a mixture of 241 g of nitric acid and 546 g of sulfuric acid. The reaction is very exothermic so that a water cooling bath was required to which ice was added occasionally to keep the temperature at 50 C. The very thick reaction mixture was stirred for an additional 2 hours and poured onto 3 liters of ice. The solid was collected by filtration and washed repeatedly with a total of 6 liters of water. After air drying, the entire sample was recrystallized from 800 ml of acetone, giving a first crop of 150.4 g mp. 162-164 C.

Molecular Weight:195.17
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:195.05315777
Monoisotopic Mass:195.05315777
Topological Polar Surface Area:83.1
Heavy Atom Count:14
Complexity:215
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes