Bromine → 4-Bromo-2-methyl-1,2-dihydro-2,7-naphthyridin-1-one

HRID 518286Notes

Reaction equation

[Br:1]Br.[CH3:3][N:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5]1=[O:14]>C(O)(=O)C>[Br:1][C:12]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5](=[O:14])[N:4]([CH3:3])[CH:13]=1

Participants

Conditions

Temperature: 15 °C

Procedure

Bromine (1.1 g, 6.87 mmol) in acetic acid (10 mL) was added dropwise to 2-methyl-2,7-naphthyridin-1-one (1.1 g, 6.87 mmol) in acetic acid (60 mL) at 10-15° C. After stirring at 15° C. for 1 h, the mixture was concentrated under vacuum. Purification by silica gel chromatography (DCM: MeOH=50:1 to 10:1) gave the title compound (0.45 g, 27.4%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 9.61 (1H, s), 8.86-8.85 (1H, d, J=5.6 Hz), 7.62-7.60 (1H, d, J=5.6 Hz), 7.56 (1H, s), 3.63 (3H, s).

Workup

concentrationthe mixture was concentrated under vacuum
customPurification by silica gel chromatography (DCM: MeOH=50:1 to 10:1)

Sources & evidence

ORD record: ord-ec687e60033d454a8a9b01b2af2a9d8c
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115114B2

Reaction notes

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