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 2069757Notes

Reaction equation

HRID 2069757 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-d1be29a32a264c1283431983127f5c0d
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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