Iodoethane → HCID 59268510, compound

HRID 2370745Notes

Reaction equation

HRID 2370745 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N:8][CH:7]=[CH:6]2.[CH2:13](B(CC)CC)[CH3:14].[K].ICC.[OH-].[Na+].[O-][O-].[Na+].[Na+]>C1COCC1.ClCCl.O>[CH2:13]([C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=[N:8][CH:7]=1)[CH3:14]

Participants

9

Reactant 5

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 14803Sodium peroxideHCID 110409786-MethoxyisoquinolineHCID 86640525HCID 86640525, compound

Product 1

HCID 59268510HCID 59268510, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

6 g of 6-Methoxy-isoquinoline (152) were dissolved in dry THF. Under argon a 1M solution of potassium triethylborane (37.7 mL) was added dropwise. The solution was stirred for five hours, then iodoethane (3.3 mL) was added dropwise. The solution was stirred overnight, cooled to 0° C. and 96 mL of 1N NaOH and 36 mL of 35% sodium peroxide were added. After gas evolution stopped, water and dichloromethane were added, the aqueous layer was extracted three times with dichloromethane the organic layer was dried over sodium sulfate and the solvent was removed in vacuo.

Workup

  1. stirringThe solution was stirred overnight
  2. extractionthe aqueous layer was extracted three times with dichloromethane the organic layer
  3. dry with materialwas dried over sodium sulfate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-06f4890e2a29409cba7597b0dae2eddc
Source dataset
uspto-grants-2014_04
Patent number
US08710228B2

Reaction notes

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