Sodium Hydroxide → 4-(5-Hydroxypyridin-3-yl)benzonitrile

HRID 1685404Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 1.9 g (9.02 mM) of 4-(5-methoxy-3-pyridinyl)benzonitrile and 6.39 g (54.2 mM) of pyridinium hydrochloride is heated at 160° C. for 5 hours. After cooling and the addition of water, the pH is adjusted to 5 with concentrated sodium hydroxide solution. The mixture is extracted with ethyl acetate and the extract is dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by chromatography on a silica column (eluent: dichloromethane/ethyl acetate 92/8; v/v, then dichloromethane/methanol 9/1; v/v) to give the expected product in the form of a beige solid with a yield of 76%.

Workup

temperatureAfter cooling
extractionThe mixture is extracted with ethyl acetate
dry with materialthe extract is dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe evaporation residue is purified by chromatography on a silica column (eluent

Sources & evidence

ORD record: ord-87ed16d436274bd0ae60be52cb000c08
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148407B2

Reaction notes

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