Water → HCID 70339160, compound

HRID 363266Notes

Reaction equation

HRID 363266 reaction equation
[F:1][C:2]1[C:11]2[C:10](=[O:12])[CH:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:8][CH2:7][C:6]=2[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:10](=[O:12])[CH:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:23][CH:22]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 136023124184696-85-3

Product 1

HCID 70339160HCID 70339160, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 mmol of 1-fluoro-3-(4-hydroxyphenyl)-7-octyl-6,7-dihydro-5H-isoquinolin-8-one 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-fluoro-3-[4-(octyloxy)phenyl]-7-octyl-6,7-dihydro-5H-isoquinolin-8-one.

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-93de1b0967d74cabbaf1b6810cdf8a85
Source dataset
uspto-grants-1999_02
Patent number
US05874023

Reaction notes

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