1-Bromo-3-chloropropane → HCID 57439896, compound

HRID 906408Notes

Reaction equation

HRID 906408 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][CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][Cl:23]>CN1C(=O)CCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:20][CH2:21][CH2:22][Cl:23])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 158851826-Bromoisoquinolin-1(2H)-one

Product 1

HCID 57439896HCID 57439896, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 6-bromoisoquinolin-1(2H)-one (Example 1b) (2 g) dissolved in NMP (20 mL) was treated with potassium carbonate (1.974 g) and 1-bromo-3-chloropropane (8.83 ml) under nitrogen. The resulting mixture was stirred at 70° C. for 10 h. The cooled reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was dried (MgSO4), and evaporated. The residue was purified (SiO2 chromatography, elution with a mixture of DCM and isohexane) to give the subtitle compound (1.70 g).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified (
  6. washSiO2 chromatography, elution
  7. additionwith a mixture of DCM and isohexane)

Sources & evidence

ORD record
ord-c34828d9a0524f4f80684cccc8a3a1a9
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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