Water → HCID 178480720, compound

HRID 2236630

Reaction equation

HRID 2236630 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]OC.[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1.O>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:30][C:27]1[CH:26]=[CH:25][C:24]([N:21]2[CH2:20][CH2:19][N:18]([CH3:17])[CH2:23][CH2:22]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Product 1

HCID 178480720HCID 178480720, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

To a suspension of crude 6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (423 mg, 1.5 mmol) in N,N-dimethylformamide (3 mL) is added 4-(4-Methyl-piperazin-1-yl)-phenylamine (290 mg, 1.5 mmol). The reaction mixture is shaken at 115° C. for 1.5 hours. Upon cooling to room temperature and addition of 2 mL of water, the product precipitated out. The precipitate is then filtered off, washed with water, and dried to yield 0.5 g of crude 6-bromo-4-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-4H-isoquinoline-1,3-dione, which is used as such for the next reaction.

Workup

  1. temperatureUpon cooling to room temperature
  2. customthe product precipitated out
  3. filtrationThe precipitate is then filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-1528c0fd74204ed9af8dc01d5c4f617b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Linked notes

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