Pyridine → 2-Amino-6-chloropyridine-3-carbonitrile

HRID 2171530Notes

Reaction equation

Cl.[NH2:2][C:3]1[C:8]([CH:9]=[N:10]O)=[CH:7][CH:6]=[C:5]([Cl:12])[N:4]=1.O1CCOCC1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[NH2:2][C:3]1[C:8]([C:9]#[N:10])=[CH:7][CH:6]=[C:5]([Cl:12])[N:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

11.15 g (53.6 mmol) of 2-amino-6-chloropyridine-3-carbaldehyde oxime hydrochloride (Example 108A) are introduced into dioxane, 13 ml (161 mmol) of pyridine are added, and the mixture is cooled to 0° C. 8.3 ml (58.95 mmol) of trifluoroacetic anhydride are added, and the reaction is allowed to warm to RT and then stirred at 60° C. for 2 h. The reaction mixture is taken up in a mixture of ethyl acetate and sodium bicarbonate solution. The organic phase is washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated in a rotary evaporator. The residue is suspended in 3:1 dichloromethane:diethyl ether, and the solid is filtered off with suction and dried. 5.56 g (66% of theory) of the product are obtained as a solid.

Workup

additionare added
temperatureto warm to RT
washThe organic phase is washed with saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulphate
concentrationconcentrated in a rotary evaporator
filtrationdiethyl ether, and the solid is filtered off with suction
customdried
custom5.56 g (66% of theory) of the product are obtained as a solid

Sources & evidence

ORD record: ord-d0b71f556db7422680cbd82bfab1aba8
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051323B2

Reaction notes

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