Hydrochloric Acid → 3-(aminomethyl)-6-methyl-4-pyridin-4-yl-1H-pyridin-2-one

HRID 593853Notes

Reaction equation

[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[C:4]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:3]=1.[BH4-].[Na+].II.Cl>C1COCC1>[NH2:10][CH2:9][C:5]1[C:6](=[O:8])[NH:7][C:2]([CH3:1])=[CH:3][C:4]=1[C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice bath cooled THF (100 mL) solution of 6-methyl-2-oxo-1,2-dihydro-4,4′-bipyridine-3-carbonitrile (4 g, 18.9 mmol) was added NaBH4 (1.43 g, 37.9 mmol), and I2 (4.81 g, 18.9 mmol), and the mixture was stirred for 0.5 h. The reaction mixture was then heated at reflux for 4 h. After cooling to 0° C., the reaction mixture was adjusted to pH 5 with 4N HCl. The mixture was concentrated in vacuo to give the crude compound, which was purified by HPLC to give 3-(aminomethyl)-6-methyl-4,4′-bipyridin-2(1H)-one (1.9 g, 31%) as a TFA salt. LCMS MH+=216.0 1H NMR (400 MHz, DMSO-d6 in D2O) δ 8.87 (d, 2H), 7.87 (d, 2H), 6.13 (s, 1H), 3.65 (br s, 2H), 2.17 (s, 3H).

Workup

temperatureThe reaction mixture was then heated
temperatureat reflux for 4 h
concentrationThe mixture was concentrated in vacuo
customto give the crude compound, which
customwas purified by HPLC

Sources & evidence

ORD record: ord-d5bda6e67c1849f0a0eabee3b03d3445
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242962B2

Reaction notes

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