Hydrochloric Acid → 6-Chloro-4-methoxypyridine-3-carbonitrile

HRID 1483700Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.[CH3:12][O-:13].[Na+].Cl>CO>[Cl:11][C:9]1[CH:8]=[C:7]([O:13][CH3:12])[C:3]([C:4]#[N:6])=[CH:2][N:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4,6-dichloro-nicotinonitrile (1) (200 mg, 1.06 mmol) in methanol (anhydrous, 10 mL) was added sodium methoxide solution (0.5 M/MeOH, 2.12 mL, 1.06 mmol). The reaction was heated at 60° C. overnight. After cooling the reaction solution to room temperature, HCl (1M, 8 mL) was added. The volatile components were evaporated in vacuo. Purification was accomplished by Biotage (10%-50% EtOAc/hexanes gradient mobile phase) to afford 150 mg (77% yield) of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.48 (s, 1H), 6.98 (s, 1H), 4.03 (s, 3H)

Workup

temperatureAfter cooling the reaction solution to room temperature
customThe volatile components were evaporated in vacuo
customPurification

Sources & evidence

ORD record: ord-090b1cda3fc5466f9499f56367fbe051
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416146B2

Reaction notes

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