Isopropyl iodide → HCID 178458418, compound

HRID 2236620Notes

Reaction equation

HRID 2236620 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.I[CH:26]([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[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]([O:23][CH:26]([CH3:28])[CH3:27])=[C:19]([OH:24])[CH:18]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 178518275HCID 178518275, compound

Product 1

HCID 178458418HCID 178458418, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (4Z)-6-bromo-4-{[(3,4-dihydroxybenzyl)-amino]methylene}isoquinoline-1,3(2H,4H)-dione (0.74 g, 1.9 mmol) in 5 mL of N,N′-dimethylformamide is added 2-iodopropane (0.19 mL, 1.9 mmol) and 0.52 g (3.8 mmol) of potassium carbonate. The reaction mixture is heated at 70° C. under N2. Mass spectroscopy indicated the completion of reaction after 3.5 h. The reaction mixture is filtered through a pad of celite, and water is added to give a precipitate. It is filtered and washed successively with MeOH, Et2O and hexane, dried in oven (60° C.) overnight to afford 0.58 g (70.7% yield) of tan solid: mp 212-213° C.; MS (ESI) m/z 431.2 and 433.2 (M+H)+1

Workup

  1. customthe completion of reaction after 3.5 h
  2. filtrationThe reaction mixture is filtered through a pad of celite, and water
  3. additionis added
  4. customto give a precipitate
  5. filtrationIt is filtered
  6. washwashed successively with MeOH, Et2O and hexane
  7. customdried in oven (60° C.) overnight

Sources & evidence

ORD record
ord-84f6e226ed1b4a6c823520721e9385e2
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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