1-(4-isopropoxy-3-methoxyphenyl)methanamine synthesis
- Product Name:1-(4-isopropoxy-3-methoxyphenyl)methanamine
- CAS Number:98799-37-2
- Molecular formula:C11H17NO2
- Molecular Weight:195.26
98799-36-1
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98799-37-2
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Yield:98799-37-2 98%
Reaction Conditions:
with sodium hydroxide in ethanol at 20; for 1.5 h;
Steps:
4.4. (4-Isopropoxy-3-methoxyphenyl)methanamine (11)
A solution of 10 (4.0 g, 20.6 mmol) in 95% ethanol (44 mL) was treated with a solution of hydroxylamine hydrochloride (1.82 g, 26.2 mmol) in dry pyridine (8.13 mL) under stirring at room temperature for 90 min, then at 0 °C for 30 min to facilitate 4-isopropoxy-3-methoxybenzaldoxime precipitation. The white solid was filtered, dried (3.20 g, 74%) and used without further purification; mp 130 °C. 1H NMR (CDCl3) δ: 8.09 (1H, s), 7.23 (1H, d, J = 1.9 Hz), 7.03 (1H, dd, J = 1.9 and 8.2 Hz), 6.89 (1H, d, J = 8.2 Hz), 4.60 (1H, m), 3.89 (3H, s,), 1.40 (6H, d, J = 6.1 Hz). A solution of the oxime (3.15 g, 15.0 mmol) in 95% ethanol (38.5 mL) was treated with an equal volume of 2 M NaOH followed by Al/Ni alloy (4 g) under stirring at room temperature for 90 min. The Al/Ni alloy was removed by filtration and washed with fresh ethanol. Filtrate and washings were combined, acidified with 0.8 M HCl (pH 2) and extracted with DCM (3 × 15 mL). The aqueous phase was treated with solid KOH up to pH 14 and extracted with diethyl ether (3 × 10 mL). The extracts, after drying over anhydrous Na2SO4 and removal of the solvent, provided 11 (2.88 g, 98%) as a brown oil. 1H NMR (CDCl3) δ: 6.90 (1H, dd, J = 2.1 and 8.2 Hz), 6.80 (1H, d, J = 8.2 Hz), 6.75 (1H, d, J = 2.1 Hz), 4.56 (1H, m), 3.89 (3H, s), 3.75 (2H, s), 1.40 (6H, d, J = 6.10 Hz).Anal. Calcd for C11H17NO2: C, 67.66; H, 8.78; N, 7.17. Found: C, 67.62; H, 8.75; N, 7.12.
References:
Cananzi, Salvatore;Merlini, Lucio;Artali, Roberto;Beretta, Giovanni Luca;Zaffaroni, Nadia;Dallavalle, Sabrina [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 16,p. 4971 - 4984] Location in patent:experimental part
98799-36-1
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$65.00/100mg
98799-37-2
12 suppliers
$45.00/25mg
2538-98-9
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$46.00/1g
98799-37-2
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$45.00/25mg
121-33-5
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$9.00/1g
98799-37-2
12 suppliers
$45.00/25mg