2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → acetic acid 2-bromo-6-(6-methylamino-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-benzyl ester

HRID 2245660Notes

Reaction equation

HRID 2245660 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([N:23](C)[CH3:24])[CH:19]=3)[C:14]2=[O:26])[C:3]=1[CH2:4][O:5][C:6](=[O:8])[CH3:7].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([NH:23][CH3:24])[CH:19]=3)[C:14]2=[O:26])[C:3]=1[CH2:4][O:5][C:6](=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 59216405Acetic acid 2-bromo-6-(6-dimethylamino-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-benzyl ester

Product 1

HCID 59216494acetic acid 2-bromo-6-(6-methylamino-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-benzyl esterYield 47.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of acetic acid 2-bromo-6-(6-dimethylamino-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-benzyl ester (224 mg, 0.482 mmol) in 5 mL 1,4-dioxane was added 2,3-dichloro-5,6-dicyano-p-benzoquinone (109 mg, 0.48 mmol). After stirring for 4 hours, this was partitioned between ethylacetate and 1M aq. NaOH. The organic layer was washed with water, washed with brine, dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution 40 to 50% ethylacetate/hexanes) to yield acetic acid 2-bromo-6-(6-methylamino-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-benzyl ester (93 mg, 0.23 mmol). MS (ESI) 404.8 (M+H)+.

Workup

  1. customthis was partitioned between ethylacetate and 1M aq. NaOH
  2. washThe organic layer was washed with water
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (gradient elution 40 to 50% ethylacetate/hexanes)

Sources & evidence

ORD record
ord-08462fc0ee9d44ad8556e85ed0dc1f5b
Source dataset
uspto-grants-2010_03
Patent number
US07683064B2

Reaction notes

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