3-(3-Fluoro-4-methoxyphenyl)-7-hydroxy-1-naphthonitrile → 3-(3-Fluoro-4-hydroxyphenyl)-7-hydroxy-1-naphthonitrile

HRID 1830682Notes

Reaction equation

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

Participants

Reactant 2

HCID 117379173-(3-Fluoro-4-methoxyphenyl)-7-hydroxy-1-naphthonitrile

HCID 21584435Pyridinium hydrochloride

Product 1

HCID 61026913-(3-Fluoro-4-hydroxyphenyl)-7-hydroxy-1-naphthonitrile

Procedure

The title compound was prepared by reacting 7-hydroxy-3-(3-fluoro-4-methoxyphenyl)-1-naphthonitrile (0.12 g, 0.41 mmol) with pyridinium HCl (3 g) according to method B to yield 0.085 g (74%) of a white solid: mp 265–269 ° C.; 1H NMR (DMSO-d6): δ 7.04–7.09 (1H, m), 7.26 (1H, dd, J=2.31 Hz, J=8.88 Hz), 7.36 (1H, d, J=2.19 Hz), 6.52 (1H, d, J=2.19 Hz), 6.52 (1H, dd, J=1.76 Hz, J=8.40 Hz), 6.71 (1H, dd, J=2.22 Hz, J=12.88 Hz), 8.01 (1H, d, J=8.97 Hz), 8.37 (1H, d, J=1.83 Hz), 8.45 (1H, d, J=1.41 Hz), 10.33 (2H, bs); MS (ESI) m/z 278 (M−H)−.

Sources & evidence

ORD record: ord-cad3791a2f134362b80f84bdb2b49706
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

Loading…