ChemicalBook CAS DataBase List 2-AMINO-5-FLUOROBENZOIC ACID ETHYL ESTER

2-AMINO-5-FLUOROBENZOIC ACID ETHYL ESTER synthesis

5synthesis methods

Product Name:2-AMINO-5-FLUOROBENZOIC ACID ETHYL ESTER
CAS Number:391-93-5
Molecular formula:C9H10FNO2
Molecular Weight:183.18

446-08-2

2-AMINO-5-FLUOROBENZOIC ACID ETHYL ESTER

391-93-5

A. Synthesis of ethyl 2-amino-5-fluorobenzoate 2-Amino-5-fluorobenzoic acid (1.0 g, 6.4 mmol) was dissolved in a mixed solvent of ethanol (15 mL) and toluene (10 mL). Several drops of concentrated sulfuric acid (H2SO4) were added as a catalyst. A Dean-Stark splitter was installed and the reaction mixture was refluxed overnight. After completion of the reaction, it was cooled to room temperature and the solvent was removed by distillation under reduced pressure. The product was purified by silica gel column chromatography (4×15 cm), and the target product was obtained in 50% yield by sequential gradient elution with chloroform/methanol (98:2, v/v, 500 mL) and (95:5, v/v, 500 mL) as eluents. Mass spectrum (ES+): m/z 184.0 ([M+H]+); 1H NMR (CDCl3) δ 7.55 (d, 1H, ArH), 7.03 (m, 1H, ArH), 6.61 (dd, 1H, ArH), 5.6 (bs, 2H, NH2), 4.33 (q, 2H, CH2), 1.40 (t, 3H, CH3).

446-08-2 Synthesis

446-08-2
397 suppliers
$14.00/5g

391-93-5
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$29.00/100mg

Yield:391-93-5 50%

Reaction Conditions:

with sulfuric acid in ethanol;toluene;

Steps:

34.A A.

A. Ethyl 2-amino-5-fluorobenzoate 2-Amino-5-fluorobenzoic acid (1.0 g, 6.4 mmol) was dissolved in ethanol (15 mL) and toluene (10 mL). Several drops of concentrated H₂SO₄ were added. The reaction was refluxed with a Dean Stark trap overnight. The reaction was cooled to rt and the solvents removed in vacuo. The product was isolated by chromatography on silica gel (4*15 cm column) eluted with chloroform/ methanol (98:2, v/v-500 mL followed by 95:5, 500 mL) in 50% yield. MS (ES+): m/z 184.0 (M+1); ¹H NMR (CDCl₃) δ 7.55 (d, 1H, ArH), 7.03 (m, 1H, ArH), 6.61 (dd, 1H, ArH), 5.6 (bs, 2H, NH₂), 4.33 (q, 2H,CH₂), 1.40 (t, 3H, CH₃).

References:

US2003/69271,2003,A1