Lithium Hydroxide → 6-(3-Cyanophenyl)nicotinic acid

HRID 602110Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[OH-].[Li+]>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of methyl 6-(3-cyanophenyl)nicotinate (300 mg, 1.26 mmol) and 2 M lithium hydroxide solution (1.89 mL) in tetrahydrofuran (30 mL) was heated at 40° C. overnight. The tetrahydrofuran was evaporated off, water (5 mL) was added and the reaction mixture was acidified to pH 6 with 2N aqueous HCl. The precipitated solid was filtered off and dried under vacuum to give 6-(3-cyanophenyl)nicotinic acid (208 mg). 1H NMR (400 MHz, DMSO-d6) ppm 7.74 (t, J=7.8 Hz, 1H), 7.96 (m, 1H), 8.23 (m, 1H), 8.36 (m, 1H), 8.49 (m, 1H), 8.55 (m, 1H), 9.15 (m, 1H), 13.5 (broad s, 1H) LCMS 225 (M+1) ELSD 1.33 minutes.

Workup

customThe tetrahydrofuran was evaporated off
additionwater (5 mL) was added
filtrationThe precipitated solid was filtered off
customdried under vacuum

Sources & evidence

ORD record: ord-d4ef6a80bd6e45d6a214323ff72212b6
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902373B2

Reaction notes

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