Ethyl Acetate → 2-Amino-5-methylpyridine-3-carbonitrile

HRID 2035728Notes

Reaction equation

[NH2:1][C:2]1[C:7](Br)=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1.[Cu][C:11]#[N:12].C(OCC)(=O)C.[OH-].[Na+]>CN(C=O)C.O>[NH2:1][C:2]1[C:7]([C:11]#[N:12])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of 2-amino-3-bromo-5-methylpyridine (3.74 g) in DMF (30 mL) was added copper(I) cyanide (4.48 g), and the mixture was stirred under microwave irradiation at 180° C. for 30 min. To the reaction mixture were added ethyl acetate and water, 1N aqueous sodium hydroxide solution (50 mL) was added and the mixture was stirred. Insoluble material was filtered off through celite. The aqueous layer and organic layer were separated, and the aqueous layer was extracted with ethyl acetate. The extract was collected, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (357 mg) as a colorless solid.

Workup

additionwas added
stirringthe mixture was stirred
filtrationInsoluble material was filtered off through celite
customThe aqueous layer and organic layer were separated
extractionthe aqueous layer was extracted with ethyl acetate
customThe extract was collected
washwashed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-d27a99018cd849bca532ddb993994a7c
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575154B2

Reaction notes

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