Water → HCID 86628217, compound

HRID 1821419Notes

Reaction equation

HRID 1821419 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[CH3:13][NH:14][CH2:15][CH2:16][OH:17].O>CS(C)=O>[OH:17][CH2:16][CH2:15][N:14]([CH3:13])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 80162-(Methylamino)ethanolHCID 762264-Fluoro-2-nitrobenzaldehyde

Product 1

HCID 86628217HCID 86628217, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-fluoro-2-nitrobenzaldehyde (0.20 g, 1.2 mmol) in DMSO (3.5 mL) was added with 2-methylaminoethanol (0.52 mL, 6.5 mmol) and stirred at 100° C. for 5.0 hours. The reaction mixture was added with water and was washed with hexane/ethyl acetate (4/1) to remove impurities. After removing the impurities, the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain 4-[N-(2-hydroxyethyl) methylamino]-2-nitrobenzaldehyde (0.20 g, 75%).

Workup

  1. washwas washed with hexane/ethyl acetate (4/1)
  2. customto remove impurities
  3. customAfter removing the impurities
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThen, the solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-8dd0fd499b684014810a8fb85a82ee13
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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