N-(4-Fluoro-3-nitrophenyl)acetamide

Step B. N-(4-Fluoro-3-nitrophenyI)acetamide 4-Fluoro-3-nitroaniline (5.0g, 32.0 mmol) was dissolved in 50 mL of DCM at 0°C containing TEA (6.7 mL, 48.0 mmol). Acetyl chloride (2.75 mL, 38.4 mmol) was added dropwise and the solution was stirred at rt overnight. The solution was washed with aqueous 5percent KHSOStep B. N-(4-FLUORO-3-NITROPHENYL) acetamide; 4-Fluoro-3-nitroaniline (5. 0G, 32.0 mmol) was dissolved in 50 mL of DCM at 0°C containing TEA (6.7 ML, 48.0 mmol). Acetyl chloride (2. 75 ML, 38.4 mmol) was added dropwise and the solution was stirred at rt overnight. The solution was washed with aqueous 5percent KHS04 solution, saturated aqueous NAHC03 solution, brine and dried over anhydrous MGS04. The product was crystallized from DCM. Yield: 5.3g (84percent) ; 1H NMR (400 MHz, CHLOROFORM-D): 8 2.04 (s, 3 H), 7.51 (dd, J=11. 23, 9.08 Hz, 1 H), 7.80 (ddd, J=9. 08, 4. 00, 2. 93 Hz, 1 H), 8.47 (dd, J=7.03, 2.73 Hz, 1 H), 10.38 (s, 1 H).; Step B. N-(4-fluoro-3-nitrophenyl) acetamide; Acetyl Chloride (2.39 mL, 33.6 mmol) was slowly added to a solution of 3-nitro-4- fluoroaniline (5.00 g, 32.0 mmol) and Et3N in DCM (500 mL) at 0°C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was washed with water, saturated NAHC03 solution, brine, dried over anhydrous MGS04 and filtered. The solvent was concentrated giving the title compound that was used for the next step without further purification. Yield : 5.65 g (87percent) ; MS (ESI) (M+H) + : 199. 1.4-Fluoro-3-nitroaniline (5.0g, 32.0 mmol) was dissolved in 50 mL of DCM at 0°C containing TEA (6.7 mL, 48.0 mmol). Acetyl chloride (2.75 mL, 38.4 mmol) was added dropwise and the solution was stirred at rt overnight. The solution was washed with aqueous 5percent KHSOStep B: N-(4-Fluoro-3-nitrophenyl)acetamide; 4-Fluoro-3-nitro-aniline (54.2 g, 0.347 mol) was added in portions to acetic anhydride (200 mL) at room temperature. The reaction mixture was stirred overnight at room temperature. The brown solid was collected and dried in vacuo to give the title compound. Yield: 67.5 g (98percent). Step B: N-(4-Fluoro-3-nitrophenyl)acetamide4-Fluoro-3-nitro-aniline (54.2 g, 0.347 mol) was added in portions to acetic anhydride (200 mL) at room temperature. The reaction mixture was stirred overnight at room temperature. The brown solid was collected and dried in vacuo to give the title compound. Yield: 67.5 g (98percent). 4-Fluoro-3-nitrophenylamine (10 g, 64.1 mmol) was added in portions to a stirred solution of acetic anhydride (35 mL, 371 mmol). The reaction mixture was stirred for 3 h at room temperature. The reaction mixture was then quenched with ice water and neutralized with solid Na4-Fluoro-3-nitro-aniline (45.0 g, 288.2 mmol) was added portionwise to acetic anhydride (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The white solid was collected and dried in vacuo to give the desired title compound (42.0 g, 70percent). 1H NMR (400 MHz, CDCl3): δ 2.23 (s, 3 H), 7.26 (m, 1 H), 7.50 (s broad, 1 H), 7.87 (m, 1 H), 8.23 (dd, J=6.44, 2.73 Hz, 1 H).Step B. N- (4-FLUORO-3-NITROPHENYL) acetamide; 4-Fluoro-3-nitro-aniline (45.0 g, 288. 2 mmol) was added portionwise to acetic anhydride (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The white solid was collected and dried in vacuo to give the title compound (42.0 g, 70percent). 1H NMR (400 MHz, CDC13) : 8 2.23 (s, 3 H), 7.26 (m, 1 H), 7.50 (s broad, 1 H), 7.87 (m, 1 H), 8.23 (dd, J=6. 44, 2. 73 Hz, 1 H).4-Fluoro-3-nitro-aniline (45.0 g, 0.288 mol) was added in portions to acetic anhydride (150 mL) at room temperature. The reaction mixture was stirred at room temperature EPO 4-Fluoro-3-nitro-aniline (45.0 g, 288.2 mmol) was added portionwise to acetic anhydride (150 mL) at room temperature. Step B. N- (4-fluoro-3-nitrophenyl) acetamide; 4-Fluoro-3-nitro-aniline (45.0 g, 0. 288 mol) was added in portions to acetic anhydride (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The white solid was collected and dried in vacuo to give the title compound (42.0 g, 70percent). 1H NMR (400 MHz, CDC13): 8 2.23 (s, 3 H), 7.26 (m, 1 H), 7.50 (s broad, 1 H), 7.87 (m, 1 H), 8.23 (DD, J=6. 44, 2. 73 Hz, 1 H).Step B. N-(4-fluoro-3-nitrophenyl)acetamide; 4-FLUORO-3-NITRO-ANILINE (45.0 g, 0.288 mol) was added portionwise to acetic anhydride (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The white solid was collected and dried ITT vacuo to give the title compound (42.0 g, 70percent). 1H NMR (400 MHz, CDC13) : 8 2.23 (s, 3 H), 7.26 (m, 1 H), 7.50 (s broad, 1 H), 7.87 (m, 1 H), 8.23 (DD, J=6. 44, 2. 73 Hz, 1 H).Step B. N- (4-fluoro-3-nitrophenyl) acetamide; 4-Fluoro-3-nitro-aniline (45.0 g, 0.288 mol) was added in portions to acetic anhydride (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The white solid was collected and dried in vacuo to give the title compound (42.0 g, 70percent). 1H NMR (400 MHz, CDC13): 8 2.23 (s, 3 H), 7.26 (m, 1 H), 7.50 (s broad, 1 H), 7.87 (m, 1 H), 8.23 (DD, J=6. 44, 2. 73 Hz, 1 H).4-Fluoro-3-nitro-aniline (45.0 g, 0.288 mol) was added in portions to acetic anhydride (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The white solid was collected and dried in vacuo to give the title compound (42.0 g, 70percent). Step B. iV-(4-fluoro-3-nitrophenyl)acetamide 4-Fluoro-3-nitro-aniline (45.0 g, 0.288 mol) was added in portions to acetic anhydride (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The white solid was collected and dried in vacuo to give the title compound (42.0 g, 70percent). 4-Fluoro-3-nitro-aniline (45.0 g, 0.288 mol) was added in portions to acetic anhydride (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The white solid was collected and dried in vacuo to give the title compound (42.0 g, 70percent). 4-Fluoro-3-nitro-aniline (45.0 g, 0.288 mol) was added in portions to acetic anhydride (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The white solid was collected and dried in vacuo to give the title compound (42.0 g, 70percent).

Molecular Weight:198.15
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:198.04407025
Monoisotopic Mass:198.04407025
Topological Polar Surface Area:74.9
Heavy Atom Count:14
Complexity:241
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes