N-bromobutanimide → 4-Bromo-6-methoxy-3-methyl-1,2-dihydroisoquinolin-1-one

HRID 606310Notes

Reaction equation

HRID 606310 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[NH:16][C:15]([CH3:22])=[CH:14]2>CC(O)=O>[Br:8][C:14]1[C:13]2[C:18](=[CH:19][CH:20]=[C:11]([O:10][CH3:9])[CH:12]=2)[C:17](=[O:21])[NH:16][C:15]=1[CH3:22]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 123270606-Methoxy-3-methylisoquinolin-1(2H)-one

Product 1

HCID 670459194-Bromo-6-methoxy-3-methyl-1,2-dihydroisoquinolin-1-oneYield 99.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

NBS (6.9 g, 40 mmol) is added in one portion to ice-cold suspension of 6-methoxy-3-methyl-2H-isoquinolin-1-one (6.7 g, 35 mmol) in AcOH (100 ml). The ice bath is removed, and after 1 h, the mixture is concentrated in vacuo. The residue is diluted with water (40 ml) and basified with 10N—NaOH to pH 12. The resulting white solid is filtered and dried to give 9.3 g of 4-bromo-6-methoxy-3-methyl-2H-isoquinolin-1-one. 1H NMR (CDCl3) 8.10 (d, 1H), 7.14 (s, 1H), 7.08 (d, 1H), 3.89 (s, 3H), 2.37 (s, 3H).

Workup

  1. customThe ice bath is removed
  2. concentrationthe mixture is concentrated in vacuo
  3. additionThe residue is diluted with water (40 ml)
  4. filtrationThe resulting white solid is filtered
  5. customdried

Sources & evidence

ORD record
ord-6e0baf08681e4d03afd0da0212a40ee1
Source dataset
uspto-grants-2011_03
Patent number
US07915288B2

Reaction notes

Loading…