2-Methoxy-6-(4-methoxyphenyl)-1-napthonitrile → 2-Hydroxy-6-(4-hydroxyphenyl)-1-naphthonitrile

HRID 895187Notes

Reaction equation

HRID 895187 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[CH:9]=2)[C:4]=1[C:21]#[N:22].Cl.[NH+]1C=CC=CC=1>>[OH:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[CH:9]=2)[C:4]=1[C:21]#[N:22]

Participants

3

Reactant 2

HCID 111970152-Methoxy-6-(4-methoxyphenyl)-1-napthonitrileHCID 21584435Pyridinium hydrochloride

Product 1

HCID 101253192-Hydroxy-6-(4-hydroxyphenyl)-1-naphthonitrile

Procedure

The title compound was prepared by reacting 2-methoxy-6-(4-methoxyphenyl)-1-napthonitrile (0.115 g, 0.397 mmol) with pyridinium HCl (4 g) at 190° C. according to method D to yield 0.025 g (24%) of a tan solid: mp>220° C.; 1H NMR (DMSO-d6): δ 6.89 (2H, d, J=8.37 Hz), 7.28 (1H, d, J=9.07 Hz), 7.63 (2H, d, J=8.42 Hz), 7.88-7.98 (2H, m), 8.12-8.16 (2H, m), 9.63 (1H, s), 11.65 (1H, bs); MS (ESI) m/z260 (M−H)−

Workup

  1. customat 190° C.

Sources & evidence

ORD record
ord-e0419426393843edad40b3bb9a483ab0
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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