Sodium Hydroxide → HCID 136167338, compound

HRID 2370746Notes

Reaction equation

HRID 2370746 reaction equation
[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13]C)[CH:11]=2)[CH:6]=[N:5][CH:4]=1)[CH3:2].B(Br)(Br)Br.[OH-].[Na+]>ClC(Cl)C>[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[N:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 59268510HCID 59268510, compound

Product 1

HCID 136167338HCID 136167338, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1.69 g of 4-Ethyl-6-methoxy-isoquinoline (153) were dissolved in dichloroethane and stirred with 1.7 mL of boron tribromide at room temperature for 3 hours and one additional hour at 40° C. The solution was poured on ice water, pH was adjusted to 9 by addition of sodium hydroxide and the solution was extracted with dichloromethane:isopropanol 3:1. The organic layer was evaporated to dryness and the product was purified by silica gel chromatography to yield 980 mg of 154. Detected Mess: 173.9 (M+H+) (ESI)

Workup

  1. customat 40° C
  2. additionThe solution was poured on ice water, pH
  3. extractionthe solution was extracted with dichloromethane:isopropanol 3:1
  4. customThe organic layer was evaporated to dryness
  5. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6851788007344da7b3f173a67ef63752
Source dataset
uspto-grants-2014_04
Patent number
US08710228B2

Reaction notes

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