Methyl iodide → 2-Methyl-2,7-naphthyridin-1-one

HRID 575556Notes

Reaction equation

[H-].[Na+].[C:3]1(=[O:13])[C:12]2[C:7](=[CH:8][CH:9]=[N:10][CH:11]=2)[CH:6]=[CH:5][NH:4]1.[CH3:14]I.[NH4+].[Cl-]>CN(C=O)C.C(OCC)(=O)C>[CH3:14][N:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][N:10]=[CH:9][CH:8]=2)[C:3]1=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (2.9 g, 72.5 mmol, 60% in oil) was added in portions to 2H-2,7-naphthyridin-1-one (3.5 g, 24.0 mmol) in dry DMF (50 mL) at 0° C. After stirring at 0° C. for 30 min, MeI (17.0 g, 118.7 mmol) was added and the mixture was stirred for an additional 30 min. Saturated aqueous NH4Cl (250 mL) and ethyl acetate (100 mL) were added. Extractive work up with ethyl acetate and purification by silica gel chromatography (DCM:MeOH=100:1 to 10:1) gave the title compound (0.5 g, 13.1%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 9.54 (1H, s), 8.64-8.62 (1H, d, J=5.6 Hz), 7.27-7.26 (1H, d, J=5.2 Hz), 7.22-7.20 (1H, d, J=5.6 Hz), 6.37-6.35 (1H, d, J=7.2 Hz), 3.54 (3H, s).

Workup

stirringthe mixture was stirred for an additional 30 min
customExtractive work up with ethyl acetate and purification by silica gel chromatography (DCM:MeOH=100:1 to 10:1)

Sources & evidence

ORD record: ord-44ba4e74ea6d440a98ebd64a5f54aa58
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034900B2

Reaction notes

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