Ethyl 4-fluoro-3-nitrobenzoate

Step 1: Step 1-1-1 4-Fluoro-3-nitrobenzoic acid (5 g, 27 mmol) was refluxed in ethanol (50 mL) and concentrated H4.1.1 4-Fluoro-3-nitrobenzoic acid (5 g, 27 mmol) was refluxed in ethanol (50 mL) and concentrated H4-Fluoro-3-nitrobenzoic acid (5 g, 27 mmol) was refluxed inethanol (50 mL) and concentrated H2SO4 (2 mL) for 8 h.After completion of reaction (as evident from TLC), thesolvent was evaporated under reduced pressure. The aqueouslayer was extracted with ethyl acetate (25 mL × 3).The organic layer was dried over Na2SO4 and concentratedunder reduced pressure to yield 1 as cream-colored powder(75percent).General procedure: The starting material, 4-fluoro-3-nitro benzoic acid was esterified in the presence of catalytic sulfuric acid in ethanol by refluxing for 6hto afford 1 in 70percent yield. Ethyl-4-fluoro-3-nitrobenzoate, 1 (0.5g, 2.34mmol) and amine (2.58mmol) [a–h: 1-(3-aminopropyl)-2-pyrrolidinone; i–p: aniline] were mixed in ethanol (5mL) and stirred at room temperature for 1h. The solvent was evaporated under reduced pressure and resuspended in ethyl acetate. The organic layer was then washed with water (10mL×3), dried over NaGeneral procedure: In a 50 mL two-necked round-bottomed flask equipped with a magnetic stirring bar, a reflux condenser and a calcium chloride drying tube was placed nicotinic acid (1 g, 8.1 mmol) suspended in boron trifluoride etherate (10 mL). The reaction mixture was stirred and heated to 120 °C overnight during which the creamy reaction mixture changed into a brownish solution. Thin layer chromatography (hexane/ethyl acetate 3:1) revealed complete reaction. The cooled reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (3 x 10 mL). The combined organic extract was washed to the end of effervescence with a saturated solution of NaHCO3. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo giving a crude yield of 1.11 g (92percent).

Molecular Weight:213.16
XLogP3:2.1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:213.04373590
Monoisotopic Mass:213.04373590
Topological Polar Surface Area:72.1
Heavy Atom Count:15
Complexity:253
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes