Ethanol → HCID 57558100, compound

HRID 1162935Notes

Reaction equation

HRID 1162935 reaction equation
C=O.[CH2:3]([OH:5])[CH3:4].OC[CH2:8][NH:9][CH2:10][C:11]([NH:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])[NH:20][C:21]2=[O:24])=[CH:16][CH:15]=1)=[O:12]>O>[OH:5][CH2:3][CH2:4][N:9]1[CH2:10][C:11](=[O:12])[N:13]([C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]([F:34])([F:33])[F:32])[NH:20][C:21]3=[O:24])=[CH:16][CH:15]=2)[CH2:8]1

Participants

5

Reactant 3

HCID 702EthanolHCID 712FormaldehydeHCID 57558171HCID 57558171, compound

Product 1

HCID 57558100HCID 57558100, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 37% formalin aqueous solution (3.8 μl, 0.0469 mmol) was added to an ethanol solution (2 ml) that contained the 2-(2-hydroxyethylamino)-N-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]acetamide (19 mg, 0.0469 mmol) obtained in step B. The obtained mixture was stirred under heating to reflux for 3 hours. Thereafter, water was added to the reaction solution, and the mixture was then extracted with ethyl acetate. The extract was washed with water and a saturated saline solution, and was then dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=25:1), so as to obtain 7-[3-(2-hydroxyethyl)-5-oxoimidazolidin-1-yl]-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (5.2 mg, 27%).

Workup

  1. temperatureunder heating
  2. temperatureto reflux for 3 hours
  3. extractionthe mixture was then extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materiala saturated saline solution, and was then dried over anhydrous sodium sulfate
  6. distillationThereafter, the solvent was distilled away under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=25:1)

Sources & evidence

ORD record
ord-776e43b43fb14d188783b7b60c11ce04
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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