Potassium Carbonate → HCID 178470085, compound

HRID 2236655Notes

Reaction equation

HRID 2236655 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([OH:24])[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:32](Br)([C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:33]([O:35][CH2:36][CH3:37])=[O:34]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]2[O:23][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])([C:38]([O:40][CH2:41][CH3:42])=[O:39])[O:24][C:19]=2[CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69427Propanedioic acid, 2,2-dibromo-, 1,3-diethyl esterHCID 178518275HCID 178518275, compound

Product 1

HCID 178470085HCID 178470085, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (Z)-6-bromo-4-((3,4-dihydroxybenzylamino)methylene)isoquinoline-1,3(2H,4H)-dione (195 mg, 0.50 mmole), dimethylformamide (5 mL), potassium carbonate (415 mg, 3.0 mmole) and diethyl 2,2-dibromomalonate (159 mg, 0.50 mmole) is stirred at room temperature overnight. The reaction mixture is filtered and washed with dimethylformamide, the filtrate is evaporated dissolved in 2% methanol in chloroform and passed through a pad of Florisil. The eluate is evaporated to give a beige solid, 114 mg, (41%), mp 222-3° C.; MS (ES+): m/z 545.1 (M+H).

Workup

  1. filtrationThe reaction mixture is filtered
  2. washwashed with dimethylformamide
  3. customthe filtrate is evaporated
  4. dissolutiondissolved in 2% methanol in chloroform
  5. customThe eluate is evaporated
  6. customto give a beige solid, 114 mg, (41%), mp 222-3° C.

Sources & evidence

ORD record
ord-5337ef8b9f9a47dea9676680e484ca45
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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