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Pharmaceutical Expertise - Certificate
Of Analysis
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Compound: 7-Hydroxy Propranolol Molecular Formula: C16H21NO3 .(mw base = 275.34)
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Structure: |
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Synonyms: (CA index name) 1-[(1-Methylethyl)amino]-3-(1-{7-hydroxy}-naphthalenyloxy)-2-Propanol |
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Summary of Analytical Results:
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Click on individual section headings
below for spectra and structure.
You may also click
here to open a printable pdf version of the complete
structure and spectra information. |
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1. |
1H NMR proton data (DMSO-d6): The
results of 1H NMR spectroscopic analysis are consistent with
the structure of 1-[(1-Methylethyl)amino]-3-(1-{7-hydroxy}-naphthalenyloxy)-2-propanol.
The aromatic region (8.4-6.6 ppm) of the 1H-NMR exhibits numerous
proton resonances. These aromatic protons are consistent with
a disubstituted naphthalenyl aromatic ring. Integration and proton-proton
coupling reveals two separate spin systems; an ABX and an ABC.
Aliphatic proton resonances are exhibited between 4.5 ppm and
1 ppm. These resonances reveal 12 protons separated into two
isolated contiguously coupled spin systems. One spin system is
an isopropyl and the second is a 1,2,3-tri-substituted propyl
spin system. All features are consistent with the structure of
7-Hydroxy Propranolol. |
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2. |
1H NMR 2-D gCOSY data
(DMSO-d6): The
data developed from the 2-D COSY experiment reveal spin-spin
3-bond (vicinal) coupling via off axis contour correlations.
The illustrated 2-D gCOSY is consistent with an isopropyl spin
system, a 1,2,3-tri-substituted propyl spin system, an aromatic
ABX and an ABC spin system. |
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3. |
1H NMR 1-D GOCSY data
(DMSO-d6): The
data developed from the 1-D GOCSY experiment (eq. TOCSY exp)
reveal isolated contiguously coupled spin systems. The illustrated
portions of the 1-D GOCSY’s are consistent with an isopropyl
spin system, an aromatic ABX and an ABC spin system. |
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The 2-D gCOSY and 1-D GOCSY data are
summarized |
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4. |
1HNMR
1-D nOe difference experimental data (DMSO-d6): The results of
1H NMR 1-D nOe difference spectroscopic
analysis are consistent with the structure of 1-[(1-Methylethyl)amino]-3-(1-{7-hydroxy}-naphthalenyloxy)-2-propanol.
These data reveal through space or proximal located spins. These
data are based upon relaxation phenomenon. Thus, pre-irradiation
of an isolated resonance reveals, via a difference spectrum,
proximal protons. |
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5. |
13C
NMR data (DMSO-d6): The data
developed from the 1-D APT Carbon experiment modulate the carbon
data based upon the one bond proton-carbon coupling (1JHC –Hz).
The data is expressed via up and down peak depending upon the
magnitude of their one bond coupling. The data are consistent
with the structure of 7-Hydroxy Propranolol. |
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6. |
1H
- 13C
NMR 2-D gHSQC data (DMSO-d6): The data developed
from the 2-D gHSQC experiment reveal one bond cross correlations
between protons and carbons in a two dimensional
format. Assignments in either domain allow direct assignment
of the opposite domain from their cross contours. The assignments
are based upon data and conclusions obtained from earlier experiments,
i.e. 2-D gCOSY, 1-D nOe difference data, 1-D APT carbon data,
chemical shifts and coupling constant considerations. The data
are consistent with the structure of 7-Hydroxy Propranolol. |
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7. |
1H
- 13C
NMR 2-D HMBC data (DMSO-d6):
The data developed from the 2-D HMBC experiment reveal 3-bond
cross correlations
between protons and carbons in a two dimensional
format. The experiment is optimized with a time delay for 8 Hz
coupling (3JHC coupling). Occasionally
a 2-bond correlation will appear. Furthermore, the suppression
on 1-bond couplings also
appears in the spectra due to non-optimal bird-pulse suppression. |
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Important 3-bond correlations are summarized in
this structural illustration: |
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8. |
IR
(HCl salt in a KBr pellet): The
Infrared data are consistent with the structure of 7-Hydroxy
Propranolol. The strongest absorbance is exhibited in the broad
band between 3480 - 3000 cm-1.
This is consistent with hydroxyl moiety in the molecule. Asymmetric
deformation modes of stretching
for the naphthenyl ring occur as bands between 1628 and 1600
cm-1, symmetric modes occur
between 1540 and 1500 cm-1.
Aromatic character is also expressed in the area between 824
-751 cm-1,
the result of out-of-plane proton-carbon bending. Aliphatic character
(2773, 2820 and 2861 cm-1) is
revealed in numerous areas of the spectrum and the strong bands
at 1101 and 1263 cm-1 are consistent
with oxygen-carbon stretching. |
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9. |
LC/UV/ESI/MS: The
sample was evaluated by HPLC/UV/ElectroSpray Ionization/MS. The
results are consistent
with the structure of 7-Hydroxy Propranolol. The molecular ion
(M+H)+ is observed at 276 Daltons along with structurally related
fragment ions. No unrelated ions were observed by mass spectrometry
under the UV peak. The % Total Area of 7-Hydroxy Propranolol
calculated at 220 nm is 99%. |
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10. |
TLC Analysis: via
Thin Layer Chromatography via Analtech Uniplate - Silica Gel
GHLF shows one spot (R.F.
= 0.37; in methylene chloride : methanol : ammonia [90:10:1]
and R.F. = 0.4; in ethyl acetate : methanol : ammonia [80 : 20
: 1]. |
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