N-bromobutanimide → 7-Benzyl-1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

HRID 409245Notes

Reaction equation

HRID 409245 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]=[C:10]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[Br:23]N1C(=O)CCC1=O>CC#N>[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]=[C:10]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 671101307-Benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

Product 1

HCID 866170717-Benzyl-1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl esterYield 12.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7-benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (1 mmol, 293 mg), N-bromosuccinimide (1.2 mmol, 214 mg) and anhydrous MeCN (10 mL) was stirred at ambient temperature for 4 days before 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 hexanes:ethyl acetate=75:25 gave the title compound as an off-white solid (48 mg); MS-(+)-ion: M+1, 79Br/81Br=372.4 and 374.4.

Workup

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

Sources & evidence

ORD record
ord-f1705bafeb224938a8f79017f0ab7e5b
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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