Diethyl Ether → 4-Bromo-5-methylisoquinolin-1(2H)-one

HRID 1470455Notes

Reaction equation

HRID 1470455 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=[O:12].[Br:13]Br.CCOCC>C(Cl)Cl>[Br:13][C:4]1[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[CH3:1])[C:7](=[O:12])[NH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 99204505-Methyl-1,2-dihydroisoquinolin-1-one

Product 1

HCID 183694934-Bromo-5-methylisoquinolin-1(2H)-oneYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-methylisoquinolin-1(2H)-one (Intermediate-3) (10 g, 63 mmol) in CH2Cl2 (100 mL) was added, Br2 (11.1 g, 69.3 mmol) drop wise and the mixture was stirred at RT (room temperature) overnight. Et2O (200 mL) was added to it, stirred for few min after which, a yellow solid precipitated out. It was filtered, washed with MeOH (10 mL), and dried to give desired intermediate (10 g, 67%) as white solid.

Workup

  1. customa yellow solid precipitated out
  2. filtrationIt was filtered
  3. washwashed with MeOH (10 mL)
  4. customdried

Sources & evidence

ORD record
ord-27de2f51c39f421e9b805e638fd9fdcf
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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