Ethyl Acetate → HCID 23363123, compound

HRID 1081870Notes

Reaction equation

HRID 1081870 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N+:15]([O-])=O)=[C:11]([CH:14]=2)[NH:12][CH3:13])=[C:4]([CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[CH:3]=1.C(OCC)(=O)C>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([NH2:15])=[C:11]([NH:12][CH3:13])[CH:14]=2)=[C:4]([CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[CH:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 23363137HCID 23363137, compound

Product 1

HCID 23363123HCID 23363123, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

5-[4-Chloro-2-(1H-imidazol-1-ylmethyl)phenoxy]-N-methyl-2-nitroaniline (250 mg) from Example 28 was dissolved in acetic acid (3 ml), followed by gradual addition of zinc powder (250 mg) at room temperature. After the addition, ethyl acetate was added to filter off insoluble materials. To the filtrate was added saturated sodium hydrogencarbonate solution carefully for separation. The organic layer was washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was purified by chromatography on a silica gel column (methylene chloride:methanol=97:3) to give 4-[4-chloro-2-(1H-imidazol-1-ylmethyl)phenoxy]-2-methylaminoaniline (160 mg; 70%).

Workup

  1. additionwas added
  2. filtrationto filter off insoluble materials
  3. additionTo the filtrate was added saturated sodium hydrogencarbonate solution
  4. customcarefully for separation
  5. washThe organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removal of the solvent under reduced pressure
  8. customthe residue was purified by chromatography on a silica gel column (methylene chloride:methanol=97:3)

Sources & evidence

ORD record
ord-dd6bf83824c041d1b5940b0948be3653
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

Loading…