Water → 4-Bromo-2-methyl-6-(6-methylpyridin-3-yl)isoquinolin-1-one

HRID 518294Notes

Reaction equation

HRID 518294 reaction equation
[Br:1]Br.[CH3:3][N:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]3[CH:15]=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=3)[CH:10]=2)[C:5]1=[O:21].O.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]3[CH:15]=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=3)[CH:10]=2)[C:5](=[O:21])[N:4]([CH3:3])[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 1180223352-Methyl-6-(6-methylpyridin-3-yl)isoquinolin-1-one

Product 1

HCID 1180216054-Bromo-2-methyl-6-(6-methylpyridin-3-yl)isoquinolin-1-oneYield 67.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (97 mg, 0.61 mmol) in acetic acid (0.61 mL) was added dropwise to 2-methyl-6-(6-methylpyridin-3-yl)isoquinolin-1-one (160 mg, 0.64 mmol) in acetic acid (6 mL) at 0° C. After stirring at room temperature for 17 min, water (22 mL) was added and the pH was adjusted to 7-8 with 1M NaOH. Extractive work up with ethyl acetate and purification by silica gel chromatography (PE:EA=2:1 to 3:2) gave the title compound (135 mg, 64.3%) as a yellow solid. LCMS: 329.0 (M+H)+

Workup

  1. customExtractive work up with ethyl acetate and purification by silica gel chromatography (PE:EA=2:1 to 3:2)

Sources & evidence

ORD record
ord-c648107c6fb248e486a50ba31dd844c9
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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