8-Chloro-3-(3-fluoro-4-methoxyphenyl)-7-hydroxy-1-naphthonitrile → 8-Chloro-3-(3-fluoro-4-hydroxy-phenyl)-7-hydroxy-naphthalene-1-carbonitrile

HRID 895259Notes

Reaction equation

[Cl:1][C:2]1[C:3]([OH:23])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]#[N:13])=[CH:9][C:8]([C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]([F:22])[CH:15]=1)=[CH:7]2.Cl.[NH+]1C=CC=CC=1>>[Cl:1][C:2]1[C:3]([OH:23])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]#[N:13])=[CH:9][C:8]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([F:22])[CH:15]=1)=[CH:7]2

Participants

Reactant 2

HCID 114728998-Chloro-3-(3-fluoro-4-methoxyphenyl)-7-hydroxy-1-naphthonitrile

HCID 21584435Pyridinium hydrochloride

Product 1

HCID 102150588-Chloro-3-(3-fluoro-4-hydroxy-phenyl)-7-hydroxy-naphthalene-1-carbonitrile

Procedure

The title compound was prepared by reacting 8-chloro-3-(3-fluoro-4-methoxyphenyl)-7-hydroxy-1-naphthonitrile (0.042 g, 0.13 mmol) with pyridinium HCl (1.8 g) according to method D to yield 0.033 g (78%) of a tan solid. This material was further purified by preparative reverse phase HPLC to yield the title compound as a white solid: mp 246-252° C.; 1H NMR (DMSO-d6): δ 7.04-7.10 (1H, m), 7.44 91H, d, J=8.94 Hz), 7.56 (1H, dd, J=1.66 Hz, J=8.37 Hz), 7.76 (1H, dd, J=2.20 Hz, J=12.88 Hz), 7.99 (1H, d, J=9.09 Hz), 8.43 (1H, d, J=1.98 Hz), 8.52 (1H, d, J=1.94 Hz), 10.19 (1H, bs), 11.05 (1H, bs); MS (ESI) m/z312/314 (M−H)−.

Sources & evidence

ORD record: ord-a958dcd369d64214ab863f851dd82d11
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914074B2

Reaction notes

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