1-Naphthylhydrazine hydrochloride synthesis
- Product Name:1-Naphthylhydrazine hydrochloride
- CAS Number:2243-56-3
- Molecular formula:C10H11ClN2
- Molecular Weight:194.66
91-59-8
2243-56-3
2.1 Synthesis of 2-naphthylhydrazine hydrochloride To a hydrochloric acid solution of 2-naphthylamine (800 mg, 5.59 mmol), a solution of sodium peroxide (Na?O?, 578 mg, 8.38 mmol) in water (1.2 mL) was slowly added under water-ice bath cooling conditions (addition time: 2 min). Subsequently, 6.0 M hydrochloric acid (6 mL) was added to the reaction system. The resulting solution was stirred in a water-ice bath for 1 h. Stannous chloride (SnCl?, 3.71 g, 19.56 mmol) was then slowly added (addition time: 5 min). The resulting suspension was continued to be stirred in a water-ice bath for 3.5 h, after which it was filtered. The filter cake was washed sequentially with water at 0 °C (4 × 8 mL), water at room temperature (1 × 8 mL), ether at 0 °C (Et?O, 2 × 4 mL), ether/hexane (1:1, 2 × 4 mL) and hexane (2 × 5 mL). The solid was dried to give 690 mg of the target product (Rf = 0.7, 40% ethyl acetate/hexane unfolding agent, milky white solid, 63% yield). 1H NMR (DMSO-d6, 250 MHz, δ): 7.81 (m, 2H, ArH), 7.71 (d, J=7.5 Hz, 1H, ArH), 7.49-7.19 (m, 4H, ArH). MS-EI+ m/z: 159.1 ([M-HCl]+).
91-59-8
204 suppliers
$54.00/100mg
2243-56-3
159 suppliers
$7.00/100mg
Yield: 63%
Reaction Conditions:
Stage #1:naphthalen-2-ylamine with hydrogenchloride;sodium nitrite in water at 0; for 1 h;
Stage #2: with tin(ll) chloride in water at 0; for 3.5 h;
Steps:
2.1; 4.1
2.1 Synthesis of 2-naphthylhydrazine hydrochlorideNaN02 (578 mg, 8.38 mmol) in H20 (1 .2 mL) was slowly added (2 min of addition) over a suspension of 2-naphthylamine (800 mg, 5.59 mmol) in HCI ac. 6.0 M (6 mL) cooled in a H20-ice bath. The resulting solution was stirred in H20-ice bath for 1 h, and SnCI2 (3.71 g, 19.56 mol) was added slowly (5 min of addition). The resulting suspension was stirred in H20-ice bath for 3.5 h, and then filtered. The solid was successively washed with H20 at 0 °C (4x8 mL), with H20 at rt (1 x8 mL), with Et20 at 0 °C (2x4 mL), with Et20/hexane (1 :1 , 2x4 mL) and with hexane (2x5 mL). The solid was dried to yield 690 mg of the desired product {Rf= 0.7 (40% AcOEt/hexane), cream solid, 63% yield). NMR-1H (DMSO-de, 250 MHz, δ): 7.81 (m, 2H, ArH); 7.71 (d, J7.49-7.19 (m, 4H, ArH).MS-EI+ m/z: 159.1 (M-HCI+1 ).
References:
LABORATORIOS DEL DR. ESTEVE, S.A.;GARCíA LóPEZ, Mónica;TORRENS JOVER, Antoni;DíAZ FERNáNDEZ, José Luis;CAAMA?O MOURE, Ana María WO2011/147910, 2011, A1 Location in patent:Page/Page column 29-30; 36-37
134-32-7
381 suppliers
$9.00/1g
2243-56-3
159 suppliers
$7.00/100mg