Ethanol → HCID 58994708, compound

HRID 606321Notes

Reaction equation

HRID 606321 reaction equation
Br[CH:2]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[C:17]([CH3:24])=[C:18]([OH:23])[CH:19]=[CH:20][C:21]=2[CH3:22])=[N:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].[CH3:25][CH2:26][OH:27]>>[CH2:26]([O:27][CH:2]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[C:17]([CH3:24])=[C:18]([OH:23])[CH:19]=[CH:20][C:21]=2[CH3:22])=[N:8][CH:7]=1)[CH2:3][CH2:4][CH3:5])[CH3:25]

Participants

3

Reactant 2

HCID 702EthanolHCID 67045907HCID 67045907, compound

Product 1

HCID 58994708HCID 58994708, compound

Procedure

A mixture of 3-[4-(1-bromo-butyl)-isoquinolin-1-yl]-2,4-dimethyl-phenol (110 mg, 0.29 mmol) and c-HCl (30 uL) in EtOH (12 ml) is heated at reflux for 18 h. After removal of solvent, the residue is diluted with DCM and neutralized with 1N—NaOH. The layers are separated and the aqueous layer is extracted with DCM. The combined organic layers are dried over Na2SO4 and concentrated. The residue is chromatographed on silica gel to give 19 mg of 3-[4-(1-Ethoxy-butyl)-isoquinolin-1-yl]-2,4-dimethyl-phenol along with the unreacted starting material (80 mg).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 h
  3. customAfter removal of solvent
  4. additionthe residue is diluted with DCM and neutralized with 1N—NaOH
  5. customThe layers are separated
  6. extractionthe aqueous layer is extracted with DCM
  7. dry with materialThe combined organic layers are dried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-d967f61211c34fa3a141e977dd1d071a
Source dataset
uspto-grants-2011_03
Patent number
US07915288B2

Reaction notes

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