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

HRID 518285Notes

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-8c3d88bea57c4f6485f2fd184406be24
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115114B2

Reaction notes

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