7-Methoxynaphthalene-1-carbonitrile → 7-Hydroxynaphthalene-1-carbonitrile

HRID 1830672Notes

Reaction equation

HRID 1830672 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[C:13]#[N:14])=[CH:5][CH:4]=1.Cl.[NH+]1C=CC=CC=1>>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[C:13]#[N:14])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 113443927-Methoxynaphthalene-1-carbonitrileHCID 21584435Pyridinium hydrochloride

Product 1

HCID 220481627-Hydroxynaphthalene-1-carbonitrile

Procedure

The title compound was prepared by reacting 7-methoxy-1-naphthonitrile (1.19 g, 6.50 mmol) with pyridinium HCl (9 g) according to method D to yield 0.88 g (80%) of a white solid: mp 184–188° C.; 1H NMR (DMSO-d6): δ 7.25 (1H, dd, J=2.30 Hz, J=8.88 Hz), 7.38 (1H, d, J=2.20 Hz), 7.39–7.44 (1H, m), 7.98 (1H, d, J=8.91 Hz), 8.04 (1H, d, J=7.14 Hz), 8.17 (1H, d, J=8.19 Hz), 10.48 (1H, s); MS (ESI) m/z 170 ([M+H]+); MS (ESI) m/z 168 (M−H)−.

Sources & evidence

ORD record
ord-19d3975fb8754e07b58d0b0e1e65aacd
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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