Bromine → 4-Bromo-2,6-dimethylisoquinolin-1-one

HRID 575568Notes

Reaction equation

HRID 575568 reaction equation
[CH3:1][N:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[C:3]1=[O:13].[Br:14]Br>C(O)(=O)C>[Br:14][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[C:3](=[O:13])[N:2]([CH3:1])[CH:11]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 140926042,6-Dimethylisoquinolin-1-one

Product 1

HCID 1180219484-Bromo-2,6-dimethylisoquinolin-1-oneYield 95.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

2,6-Dimethylisoquinolin-1-one (120.0 mg, 0.60 mmol) in acetic acid (4 mL) was treated with Br2 (96 mg, 0.6 mmol) in acetic acid (0.6 mL) at 0° C. in a manner similar to Example 72, step 2. Isolation, also in a similar manner, gave the title compound (145.0 mg, 82.9%) as a white yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.33 (d, J=8.0 Hz, 1H), 7.60 (s, 1H), 7.37 (d, J=8.0 Hz, 1H), 7.35 (s, 1H), 3.60 (s, 3H), 2.54 (s, 3H). LCMS: 252.1 (M+H)+

Sources & evidence

ORD record
ord-d4d4a514b43a438d800dc71190d998b6
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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