Sodium Hydroxide → HCID 57647053, compound

HRID 1022873

Reaction equation

HRID 1022873 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.[F:13][C:14]([F:20])([F:19])[CH2:15][CH2:16][CH2:17]I.[OH-].[Na+].[O-][O-].[Na+].[Na+]>O1CCCC1.ClCCl>[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]=[C:6]2[CH2:17][CH2:16][CH2:15][C:14]([F:20])([F:19])[F:13]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 14803Sodium peroxideHCID 27751891,1,1-Trifluoro-4-iodobutaneHCID 110409786-Methoxyisoquinoline

Product 1

HCID 57647053HCID 57647053, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2 g 6-Methoxy-isoquinoline were dissolved in 25 mL of dry tetrahydrofuran. 12.56 mL of a 1 M solution of potassium triethyl borohydrate were added dropwise. The solution was allowed to stir at room temperature for 2 h, then 3.29 g of 4,4,4-Trifluoro-1-iodobutane were added dropwise. The solution was allowed to stir overnight, then 32 mL of 1M sodium hydroxide and 12 mL of sodium peroxide solution (35%) were added. Stirring was continued for another 3 hrs, then the solution was diluted with dichloromethane, extracted with water and brine and the organic layer was dried over sodium sulfate and evaporated to dryness. Silica gel chromatography yields 1.03 g of the desired product.

Workup

  1. stirringto stir overnight
  2. stirringStirring
  3. waitwas continued for another 3 hrs
  4. extractionextracted with water and brine
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-578f06296ec841fd9fd8fe9cf661762b
Source dataset
uspto-grants-2014_05
Patent number
US08722671B2

Linked notes

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