2-Bromopropane → HCID 86683213, compound

HRID 1852138Notes

Reaction equation

HRID 1852138 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:13]2[C:8](=[C:9]([Cl:14])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([OH:15])[N:5]=1.Br[CH:17]([CH3:19])[CH3:18]>O>[Cl:3][C:4]1[C:13]2[C:8](=[C:9]([Cl:14])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([O:15][CH:17]([CH3:19])[CH3:18])[N:5]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 178515367HCID 178515367, compound

Product 1

HCID 86683213HCID 86683213, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (103 mg, 2.57 mmol) was added to a solution of 1,5-dichloroisoquinolin-3-ol (500 mg, 2.336 mmol) and 2-bromopropane (575 mg, 4.67 mmol) and stirred at rt for 3 hrs. The reaction was diluted with water and extracted with EtOAc. The organic layer was washed with water (2×) followed by brine. The organic layer was collected, dried over MgSO4, filtered and evaporated to give the crude product 1,5-dichloro-3-isopropoxyisoquinoline (598 mg, 100% yield) which was used as is in next step. MS: MS m/z 256.1(M++1).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water (2×)
  3. customThe organic layer was collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0018aed9bd8e46a3bc47d288c7c20eb3
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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