ChemicalBook CAS DataBase List 1-NAPHTHALENEACETHYDRAZIDE

1-NAPHTHALENEACETHYDRAZIDE synthesis

4synthesis methods

Product Name:1-NAPHTHALENEACETHYDRAZIDE
CAS Number:34800-90-3
Molecular formula:C12H12N2O
Molecular Weight:200.24

2876-78-0
178 suppliers
$10.00/5g

34800-90-3
101 suppliers
$5.00/250mg

Yield: 98%

Reaction Conditions:

with hydrazine hydrate in ethanol at 85; for 24 h;

Steps:

2.3. Synthesis of compound NTH
Methyl 1-naphthaleneacetate (1.0 g, 5.0 mmol) and hydrazine hydrate(≥85%, 0.8 g, 20.0 mmol) were dissolved in ethanol (100 mL). Themixture was stirred at 85 °C for 24 h. After the reaction finished, thesolvent was removed under reduced pressure and the residue wasrecrystallized in alcohol. Washed by alcohol and water afforded NTH(0.98 g, 98%) as a white needle-like solid: m.p. 181-182 °C; 1H NMR(Fig. S1) (600 MHz, CDCl3) δ (ppm): 7.92-7.91 (d, J = 6 Hz, 1 H, ArH),7.88-7.87 (d, J = 6 Hz, 1 H, ArH), 7.83-7.82 (d, J = 6 Hz, 1 H, ArH),7.56-7.50 (d, J = 30 Hz, 2 H, ArH), 7.45-7.42 (t, J = 18 Hz, 1 H, ArH),7.39-7.38 (d, J = 6 Hz, 1 H, ArH), 6,56 (s, 1H, NH), 4.03 (s, 2H, NH2),3.75-3.74 (d, J = 6 Hz, 2H, CH2); 13C NMR (Fig. S2) (151 MHz, CDCl3) δ (ppm):171.38, 133.96, 131.89, 130.02, 128.86, 128.65, 128.35, 126.90,126.24, 125.56, 123.53, 39.91; HR-MS calculated for (C12H13N2O+)[NTH + H]+ (m/z): 201.1028. Found: 201.1022 (Fig. S3).

References:

Dai, Xin-Yu;Lin, Qi;Qu, Wen-Juan;Wei, Tai-Bao;Yao, Hong;Zhang, You-Ming;Zhao, Qi [Dyes and Pigments,2021,vol. 184]