ChemicalBook CAS DataBase List 4-Benzyloxyphenylhydrazine hydrochloride

4-Benzyloxyphenylhydrazine hydrochloride synthesis

6synthesis methods

Product Name:4-Benzyloxyphenylhydrazine hydrochloride
CAS Number:52068-30-1
Molecular formula:C13H15ClN2O
Molecular Weight:250.72

51388-20-6 Synthesis

51388-20-6
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4-Benzyloxyphenylhydrazine hydrochloride

52068-30-1
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Yield:52068-30-1 96%

Reaction Conditions:

Stage #1: 4-benzyloxyaniline hydrochloridewith hydrogenchloride;sodium nitrite in water at 0; for 0.5 h;
Stage #2: with tin(ll) chloride in water at 0; for 1 h;

Steps:

(4-(Benzyloxy)phenyl)hydrazine hydrochloride (2).; Note: The reaction mixture and all added solutions were maintained at 0 °C during this procedure. 4-Benzyloxyaniline hydrochloride (3.00 g, 12.5 mmol) was added to cone. aq. HC1 (25 mL) and stirred for 10 min at 0 °C, followed by dropwise addition of a solution of NaN0₂ (852 mg, 12.3 mmol) in water (6 mL) over the course of 15 min. The mixture was stirred for an additional 15 min-period and then a solution of SnCl₂ (6.40 g, 33.1 mmol) in cone. aq. HC1 (7.5 mL) was added dropwise. The reaction mixture was stirred for 1 h and filtered to yield an off-white precipitate, which was washed with water and triturated with Et₂0, to yield 2 (3.01 g, 96%):IR (ATR, neat) 3232, 2906 (br), 2693, 1568, 1508, 1242, 1177 cm^"1; 1H NMR (DMSO-d₆, 600 MHz) δ 10.11 (bs, 3 H), 7.44-7.40 (m, 2 H), 7.40-7.35 (m, 2 H), 7.33-7.29 (m, 1 H), 7.01-6.93 (m, 4 H), 5.05 (s, 2 H); ¹³C NMR (DMSO-d₆, 150 MHz) δ 153.7, 139.1, 137.3, 128.5, 128.4, 128.3, 127.9, 127.7, 127.5, 117.1, 116.9, 115.5, 115.3, 69.5; HRMS (EI) m/z calcd for Ci₃Hi₄N₂0 214.1106, found 214.1110.