ETHYL 4-HYDROXYBENZIMIDATE HYDROCHLORIDE synthesis
- Product Name:ETHYL 4-HYDROXYBENZIMIDATE HYDROCHLORIDE
- CAS Number:54998-28-6
- Molecular formula:C9H12ClNO2
- Molecular Weight:201.65
Yield: 97%
Reaction Conditions:
with hydrogenchloride
Steps:
11
4-[Imino(ethoxy)methyl]phenol hydrochloride; 4-Cyanophenol (2.2 g, 18.5 mmol) was suspended in dry ethanol (40 ml). Dry hydrogen chloride gas was bubbled through the solution for 40 min and the resulting mixture protected with a calcium chloride drying tube and stirred overnight. After evaporation, the white solid that remained was triturated with dry diethyl ether and filtered under nitrogen to give the title phenol (3.6 g, 97%), mp 173°. 1H NMR (300 MHz, DMSO-d6) δ 1.44 (t, J = 6.6 Hz, 3H, CH3), 4.56 (q, 2H, J = 6.8 Hz, 2H, CH2), 6.99 (d, J = 8.8 Hz, 2H, H2, 6), 8.01 (d, J = 8.8 Hz, 2H, H3, 5). 13C NMR (75.2 MHz, DMSO-d6) δ 13.6 (CH3), 69.1 (CH2), 115.4, 116.1, 131.7, 164.5, 170.1. MS (FAB, thioglycerol) 166 (M+H, -HCl).
References:
Peter MacCallum Cancer Institute EP2044938, 2009, A2 Location in patent:Page/Page column 26
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