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

HRID 2077158Notes

Reaction equation

HRID 2077158 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][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[O:4].[Br:25]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:25])[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][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 671102494-Hydroxy-8-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester

Product 1

HCID 866170691-Bromo-4-hydroxy-8-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl esterYield 85.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-hydroxy-8-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester (1.17 mmol, 381 mg), N-bromosuccinimide (1.3 mmol, 234 mg), benzoyl peroxide (0.06 mmol, 15 mg), and CCl4 (8 mL) was refluxed with stirring for 2.5 h. After cooling to ambient temperature silica gel was added and the mixture was concentrated in vacuo. The residue was added on top of a chromatography column filled with silica gel. Elution with CH2Cl2 gave the title compound as a tan solid (403 mg); MS-(+)-ion: M+1, 79Br/81Br=404.3 and 406.3.

Workup

  1. temperaturewas refluxed
  2. additionwas added
  3. concentrationthe mixture was concentrated in vacuo
  4. additionThe residue was added on top of a chromatography column
  5. additionfilled with silica gel
  6. washElution with CH2Cl2

Sources & evidence

ORD record
ord-3bcbad07dc694f3887f101dbd05b27a2
Source dataset
uspto-grants-2011_04
Patent number
US07928120B2

Reaction notes

Loading…