ChemicalBook CAS DataBase List Methyl 4-amino-3-(benzyloxy)benzoate

Methyl 4-amino-3-(benzyloxy)benzoate synthesis

6synthesis methods

Product Name:Methyl 4-amino-3-(benzyloxy)benzoate
CAS Number:475215-88-4
Molecular formula:C15H15NO3
Molecular Weight:257.28

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Yield:475215-88-4 100%

Reaction Conditions:

with iron⁽⁰⁾;glacial acetic acid at 20 - 40; for 4 h;

Steps:

4.11. Methyl 4-amino-3-benzyloxybenzoate (9b)

Iron powder (2.62 g, 46.9 mmol) was added carefully to a solution of methyl 3-benzyloxy-4-nitrobenzoate (20) (1.35 g, 4.69 mmol) in glacial acetic acid (20 mL). The resulting mixture was stirred for 2 h at room temperature and then for 2 h at 40 °C. The suspension was filtered with ethyl acetate over Hyflo Super Cel medium and the solvents were removed under reduced pressure. Water was added to the residue and the mixture was extracted four times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate and the solvents were removed under reduced pressure. Purification of the residue by flash chromatography on silica gel (petroleum ether/ethyl acetate 4:1) afforded methyl 4-amino-3-benzyloxybenzoate (9b) as colourless solid, yield: 1.21 g (100%), mp 99-100 °C (lit.:³⁵ 99-101 °C).UV (MeOH): λ_max=230, 278 (sh), 306 nm. IR (ATR): ν=3475, 3447, 3353, 3199, 3080, 3024, 2985, 2945, 1681, 1618, 1578, 1522, 1499, 1438, 1399, 1363, 1315, 1298, 1264, 1219, 1186, 1148, 1106, 1016, 994, 927, 905, 889, 841, 824, 789, 765, 736, 692, 626 cm^-1. ¹H NMR (500 MHz, CDCl₃): δ=3.86 (s, 3H), 4.20 (br s, 2H), 5.12 (s, 2H), 6.69 (dd, J=6.7, 2.0 Hz, 1H), 7.36 (tt, J=7.2, 2.5 Hz, 1H), 7.41 (tt, J=8.0, 2.2 Hz, 2H), 7.46 (d, J=7.4 Hz, 2H), 7.56 (m, 1H), 7.57 (dd, J=6.7, 1.8 Hz, 1H). ¹³C NMR and DEPT (125 MHz, CDCl₃): δ=51.86 (CH₃), 70.65 (CH₂), 112.72 (CH), 113.41 (CH), 119.54 (C), 124.50 (CH), 127.97 (2 CH), 128.34 (CH), 128.75 (2 CH), 136.74 (C), 141.51 (C), 145.38 (C), 167.39 (CO). MS (EI): m/z (%)=257 (34, M⁺), 226 (6), 166 (44), 138 (9), 91 (100), 79 (6), 65 (9), 52 (5). Anal. Calcd (%) for C₁₅H₁₅NO₃: C 70.02, H 5.88, N 5.44. Found: C 69.86, H 5.92, N 5.35.