Propranol Analysis
Recent discoveries have shown the possibility of using propranolol, a drug
commonly used to treat hypertension, to treat patients with autism. Inderal LA
(propranolol hydrochloride) is manufactured largely by ANI Pharmaceuticals Inc.
(U. S. Food and Drug Administration). The IUPAC name for propranolol is 1
naphthalen 1 yloxy 3 (propan 2 ylamino)propan 2 ol (National Center for
Biotechnology Information). Figure 1 shows the structure of propranolol
hydrochloride, which is the active component sold in pharmaceutical the industry.
Propranolol s use is to provide a reduction in resting heart rate, cardiac output,
systolic and diastolic blood pressure, and reflex orthostatic hypotension. Propranolol
is able to do this because it competes... Show more content on Helpwriting.net ...
Starting from Naphthalene, the following synthetic strategy, Figure 5, was created
using techniques discovered by the national chemical laboratory. Step one is the
addition of an alcohol group to Naphthalene using Toluene and 4 monooxygenase
(Copley, S. D). Once 1 naphthanol is the starting material used by the nation
chemical laboratory to synthesis propranolol. The following synthetic strategy is
used to create propranolol from 1 naphthol: (a) 3 bromopropanol, 10% aq NaOH,
reflux, 6 h, 67%; (b) IBX, DMSO, rt, 2 h, 89%; (c) PhNO, L proline, CH3CN, 20
В°C, 24 h then NaBH4, MeOH, 20 В°C, 0.5 h; (d) 10% Pd/C, MeOH, H2, rt, 6 h,
for two steps 79%; (e) PPh3, DIAD, reflux, 6 h, 67%; (f) isopropylamine, CH2Cl2,
rt, 12 h, 83%; (g) Et2O, HCl gas, 1 h, 86% (Panchgalle, S. P.). Some of the
important steps in this synthetic strategy is using 1 naphthol because it is a cheap
and readily available starting material. Also this procedure produces high yields and
is not harmful to the environment (Panchgalle, S. P.). Figure 6 and 7 are mechanisms
for the conversion of naphthalene to 1 naphthol by toluene 4 monooxygenase, and
the reaction labeled a in