2-hydroxynaphthalene-1-carbaldehyde [(2-hydroxy-1-naphthyl)methylene]hydrazone synthesis
- Product Name:2-hydroxynaphthalene-1-carbaldehyde [(2-hydroxy-1-naphthyl)methylene]hydrazone
- CAS Number:2387-03-3
- Molecular formula:C22H16N2O2
- Molecular Weight:340.3746
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Yield:2387-03-3 94%
Reaction Conditions:
with hydrazine in ethanol; for 3 h;Reflux;
Steps:
2.3. Synthesis of Chemosensor ADA
To a stirred solution of 2-hydroxy-1-naphthaldehyde (1.72 g,10.0 mmol), hydrazine (0.16 g, 5.0 mmol) in 30 mL ethanol wasadded and continuously stirred. After refluxing for 3 h, the mixturewas cooled to room temperature. A yellow precipitate isolated fromthe reaction mixture by filtration, then washed with EtOH for threetimes and dried. The desired compound ADA was obtained as a light yellowsolid (1.60 g, 4.70mmol, 94% yield). 1H NMR (400MHz, DMSO-d6)δ = 12.89 (s, 2H), 10.01 (s, 2H), 8.67 (d, J = 12.0 Hz, 2H), 8.06 (d, J =12.0 Hz, 2H), 7.94 (d, J = 8.0 Hz, 2H), 7.63 (t, J = 12.0 Hz, 2H), 7.45 (t,J = 12.0 Hz, 2H), 7.31 (d, J = 8.0 Hz, 2H). 13C NMR (100 MHz, DMSO-d6) δ = 151.73, 148.60, 145.97, 143.09, 131.07, 130.62, 130.02, 122.46,117.99, 112.63, 110.69; FT-IR (KBr, cm-1) ν = 3409 (OH), 1614(C_N), 1579 (C_C); HRMS (ESI): m/z [M + H]+ calcd for:C22H16N2O2: 341.1212, found 341.1254.
References:
Sun, Tao;Niu, Qingfen;Li, Tianduo;Guo, Zongrang;Liu, Haixia [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2018,vol. 188,p. 411 - 417]
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