N-bromobutanimide → HCID 23084641, compound

HRID 1783295Notes

Reaction equation

HRID 1783295 reaction equation
[CH3:1][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7]([O:15][CH2:16][O:17][CH3:18])=[N:6][C:5]=2[N:4]([CH3:19])[N:3]=1.[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:20][CH2:1][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7]([O:15][CH2:16][O:17][CH3:18])=[N:6][C:5]=2[N:4]([CH3:19])[N:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 23084861HCID 23084861, compound

Product 1

HCID 23084641HCID 23084641, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

1,3-Dimethyl-5-methoxymethoxy-3H-pyrazolo[3,4-c]isoquinoline (1.03 g), N-bromosuccinimide (0.72 g) and benzoyl peroxide (0.05 g) were dissolved in carbon tetrachloride (20 mL), and the mixture was heated under reflux for 4 hrs. After the completion of the reaction, the reaction mixture was cooled to room temperature, washed with saturated aqueous sodium hydrogen carbonate and dried over magnesium sulfate. The solvent was evaporated. The obtained solid was collected by filtration and washed with ether to give 1-bromomethyl-3-methyl-5-methoxymethoxy-3H-pyrazolo[3,4-c]isoquinoline (1.0 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. customAfter the completion of the reaction
  4. washwashed with saturated aqueous sodium hydrogen carbonate
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. filtrationThe obtained solid was collected by filtration
  8. washwashed with ether

Sources & evidence

ORD record
ord-7fd17aec7f0a4092953b0d83d57d440f
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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