1,4-Dioxane → 4-(5-(aminomethyl)-3-methylpyridin-2-yl)pyridin-2(1H)-one

HRID 711270Notes

Reaction equation

HRID 711270 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH2:15][NH2:16])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[O:17]1CCOCC1>O.Cl>[NH2:16][CH2:15][C:11]1[CH:12]=[C:13]([CH3:14])[C:8]([C:6]2[CH:5]=[CH:4][NH:3][C:2](=[O:17])[CH:7]=2)=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 67208684(2'-Fluoro-3-methyl-2,4'-bipyridin-5-yl)methanamine

Product 1

HCID 672086834-(5-(aminomethyl)-3-methylpyridin-2-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of (2′-fluoro-3-methyl-2,4′-bipyridin-5-yl)methanamine 66-1 (65 mg, 0.30 mmol) in dioxane (0.6 mL) and H2O (0.2 mL) was added a few drops of aqueous concentrated HCl solution. The mixture was stirred at 90° C. for 10 hours, and then concentrated to dryness by rotary evaporation to give 4-(5-(aminomethyl)-3-methylpyridin-2-yl)pyridin-2(1H)-one 66-2 as yellow solid.

Workup

  1. concentrationconcentrated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-474afa6e6b3b4708b593eee9c480007d
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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