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

HRID 42474Notes

Reaction equation

HRID 42474 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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 4311764Sodium borohydrideHCID 14199246HCID 14199246, compound

Product 1

HCID 674681673-(aminomethyl)-6-methyl-4-pyridin-4-yl-1H-pyridin-2-oneYield 46.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

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

Sources & evidence

ORD record
ord-530d4daea6814110a24efd5b240b71ee
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Reaction notes

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