(4-Chloro-2-methoxy-phenyl)-hydrazine hydrochloride synthesis
- Product Name:(4-Chloro-2-methoxy-phenyl)-hydrazine hydrochloride
- CAS Number:1567373-49-2
- Molecular formula:C7H10Cl2N2O
- Molecular Weight:209.07
93-50-5
1567373-49-2
The general procedure for the synthesis of (4-chloro-2-methoxyphenyl)hydrazine hydrochloride from 4-chloro-2-methoxyaniline is as follows: 4-chloro-2-methoxyaniline (1.69 g, 10.7 mmol, 1 eq.) was suspended in a mixture of concentrated hydrochloric acid (25 mL) and acetic acid (10 mL) at 0 °C. A solution of sodium nitrite (740 mg, 10.7 mmol, 1 equiv) in water (10 mL) was added slowly and dropwise. The reaction mixture was gradually warmed to 60 °C and maintained at this temperature for 1.5 hours. Subsequently, the reaction solution was cooled to 0 °C and a concentrated hydrochloric acid (25 mL) solution of stannous chloride (5.32 g, 23.6 mmol, 2.2 equiv) was added. After 30 min of reaction, the precipitate was collected by filtration to afford the target product (4-chloro-2-methoxyphenyl)hydrazine hydrochloride (2.06 g, 93% yield). The product was characterized by 1H NMR (DMSO-d6): δ 9.94 (br.s, 2H), 7.72 (br.s, 1H), 7.07 (s, 1H), 7.00 (s, 2H), 3.85 (s, 3H). With reference to the above method, other intermediates of similar structure can be prepared by substituting appropriate reagents, raw materials and purification methods.
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Yield:1567373-49-2 93%
Reaction Conditions:
Stage #1: 4-chloro-o-anisidinewith hydrogenchloride;acetic acid;sodium nitrite in water at 0 - 60; for 1.5 h;
Stage #2: with hydrogenchloride;tin(ll) chloride in water at 0; for 0.5 h;
Steps:
7.B
General procedure: B. To a suspension of compound 7b (1 .69 g, 10.7 mmol, 1 eq) in concentrated HCl (25 mL) and acetic acid (10 mL) at 0 °C was added a solution of sodium nitrite (740 mg, 10.7 mmol, 1 eq) in water (10 mL) dropwise. The suspension was warmed to 60 °C for 1.5 hrs. The solution was cooled to 0 °C and a solution of SnCl2 (5.32 g, 23.6 mmol, 2.2 eq) in concentrated HCl (25 mL) was added. After 30 minutes, a precipatate was collected by filtration to give compound 7c (2.06 g, 93%). 1H NMR (DMSO-d6) δ: 9.94 (br. s., 2H), 7.72 (br. s., 1H), 7.07 (s, 1H), 7.00 (s, 2H). 3.85 (s, 3H). Following the procedure described above for Example 7 and substituting the appropriate reagents, starting materials and purification methods known to those skilled in the art, the following intermediates to compounds of the present invention were prepared:
References:
WO2014/28805,2014,A1 Location in patent:Page/Page column 65; 66