Water → HCID 15340167, compound

HRID 1418244Notes

Reaction equation

HRID 1418244 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:10]=2[F:12])[CH:5]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[N:3]=1.[H-].[Na+].[CH2:30](Br)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].O>CN(C=O)C>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:10]=2[F:12])[CH:5]=[C:4]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:25][CH:26]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 136093201HCID 136093201, compound

Product 1

HCID 15340167HCID 15340167, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 mmol of 1,8-difluoro-3-(4-hydroxyphenyl)-7-octylisoquinoline are dissolved in 50 ml of DMF, and 11 mmol of sodium hydride are added. After the mixture has been stirred for 30 minutes, 11 mmol of 1 -octyl bromide are added dropwise, and the mixture is stirred at 60° C. for a further 140 minutes and poured into water. The mixture is extracted with dichloromethane, the combined organic phases are dried, the solvent is removed in vacuo and the residue is chromatographed on silica gel, giving 8 mmol of 1,8-difluoro-3-[4-(octyloxy)phenyl]-7-octylisoquinoline.

Workup

  1. stirringthe mixture is stirred at 60° C. for a further 140 minutes
  2. extractionThe mixture is extracted with dichloromethane
  3. customthe combined organic phases are dried
  4. customthe solvent is removed in vacuo
  5. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-4bb42890a36f4ed190b5c67e6740a2a1
Source dataset
uspto-grants-1999_03
Patent number
US05882546

Reaction notes

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