Ethyl Acetate → HCID 66808429, compound

HRID 607213Notes

Reaction equation

HRID 607213 reaction equation
Cl[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C)C=O>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 90154-MethoxyphenolHCID 10796Cesium carbonateHCID 124774-Chloro-3-nitroaniline

Product 1

HCID 66808429HCID 66808429, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-3-nitro aniline (1.0 g, 5.79 mmol), 4-methoxyphenol (0.74 g, 6.00 mmol), cesium carbonate (1.95 g, 6.00 mmol) in dimethylformamide (10 ml) was heated at 100° C. for 16 hours. Afterwards ice water (50 mL) was added to the solution and the resultant slurry was treated with ethyl acetate (100 ml). The layers were separated and the organic layer was washed with 10% sodium bicarbonate and 10% sodium chloride, then dried over anhydrous sodium sulfate. The drying agent was filtered and solvent was removed under vacuum leaving a red solid as the title compound (1.1 g, 73%).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with 10% sodium bicarbonate and 10% sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered
  5. customsolvent was removed under vacuum

Sources & evidence

ORD record
ord-46efc85f71bb44378b33374916522f3c
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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