N-bromobutanimide → 4-Bromo-6-methoxyisoquinolin-1(2H)-one

HRID 1852238Notes

Reaction equation

HRID 1852238 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH:7]=[CH:6]2.C1C(=O)N([Br:21])C(=O)C1>C(#N)C>[Br:21][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9](=[O:13])[NH:8][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 218898546-methoxyisoquinolin-1(2H)-one

Product 1

HCID 579564624-Bromo-6-methoxyisoquinolin-1(2H)-oneYield 55.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-methoxyisoquinolin-1(2H)-one (2.5 g, 14.27 mmol) in acetonitrile (10 ml) was added NBS (2.54 g, 14.27 mmol) at room temperature under argon atmosphere. The reaction mass was stirred at the same temperature for 2 h. The precipitated solid was filtered to get crude compound (2 g, 55.2%). The crude compound was taken to the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.41 (s, 1H), 8.17-8.15 (d, J=8 Hz, 1H), 7.53 (s, 1H), 7.19-7.11 (m, 2H), 3.93 (s, 3H); MS: MS m/z 256.06 (M++2).

Workup

  1. filtrationThe precipitated solid was filtered

Sources & evidence

ORD record
ord-0dfb9059130f4c95b49aeca4e9f7041c
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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