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

HRID 1616839Notes

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 4 N 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-1b3ce6289d41496d9c80463eb929f024
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765792B2

Reaction notes

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