N-bromobutanimide → 1-Bromo-4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

HRID 409198Notes

Reaction equation

HRID 409198 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:4].[Br:23]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([Br:23])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 671108484-Hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

Product 1

HCID 866170621-Bromo-4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl esterYield 97.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (103 mg, 0.35 mmol), N-bromosuccinimide (65 mg, 0.37 mmol), benzoyl peroxide (4.2 mg, 0.02 mmol), and carbon tetrachloride (2.5 mL) was refluxed for 4 h before it was cooled to room temperature and filtered. The filtrate was washed with water, saturated aqueous sodium bicarbonate solution, and brine before it was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (128 mg): MS: (+) m/z 374.0, 376.0 (M+1, 79Br/81Br), MS: (−) m/z 372.1, 374.1 (M−1, 79Br/81Br).

Workup

  1. temperaturewas refluxed for 4 h before it
  2. filtrationfiltered
  3. washThe filtrate was washed with water, saturated aqueous sodium bicarbonate solution, and brine before it
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81cc910aa2664c178ad9c88469d2a55c
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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