3-Nitrophenol → HCID 19047749, compound

HRID 1780824Notes

Reaction equation

HRID 1780824 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.CCCCCC.CCOC(C)=O>CN(C)C=O>[C:15]1([CH2:14][O:10][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][CH:7]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 111373-NitrophenolHCID 24758Sodium hydrideHCID 1378441-(Bromomethyl)naphthaleneHCID 21226206Ethyl acetate hexane

Product 1

HCID 19047749HCID 19047749, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-nitrophenol (200 mg) in 4.0 mL of dimethylformamide at 0° C. was added NaH. After 10 minutes, 1-bromomethylnaphthalene (480 mg) was added, and the cold bath was removed. After ca. 15 h, the solution was quenched by the addition of sat. NH4Cl solution, and concentrated to dryness in vacuo. The residue was diluted with ethyl acetate and washed with water, sat. aq. NaHCO3 solution, and brine. The solution was dried (MgSO4), filtered, and concentrated in vacuo to provide the crude product. Trituration with 9:1 hexane/EtOAc provided the titled compound as a light brown solid.

Workup

  1. customthe cold bath was removed
  2. waitAfter ca. 15 h
  3. customthe solution was quenched by the addition of sat. NH4Cl solution
  4. concentrationconcentrated to dryness in vacuo
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with water, sat. aq. NaHCO3 solution, and brine
  7. dry with materialThe solution was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto provide the crude product

Sources & evidence

ORD record
ord-c40920bb3fce4559a149b5cb8cb269a2
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

Loading…