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

HRID 575557Notes

Reaction equation

HRID 575557 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

4

Reactant 2

HCID 24408BromineHCID 898703502-Methyl-2,7-naphthyridin-1-one

Product 1

HCID 1180220834-Bromo-2-methyl-1,2-dihydro-2,7-naphthyridin-1-oneYield 27.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

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.

Workup

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

Sources & evidence

ORD record
ord-b908580d42d54f9b8d97e45e878b94eb
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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