HCID 5025789, compound → HCID 24709532, compound

HRID 1786843Notes

Reaction equation

HRID 1786843 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:3]=1[O:4][CH2:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[C:8]#[N:9].[Cl-].[Ca+2].[Cl-]>C(O)C.O>[NH2:18][C:16]1[CH:15]=[CH:14][C:3]([O:4][CH2:5][C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[C:8]#[N:9])=[C:2]([Cl:1])[CH:17]=1

Participants

4

Reactant 2

HCID 5025789HCID 5025789, compoundHCID 5284359Calcium Chloride

Product 1

HCID 24709532HCID 24709532, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-[(2-chloro-4-nitrophenoxy)methyl]benzonitrile (2.0 g) in ethanol/water (9:1, 40 mL) was added calcium chloride (90%, 427 mg), and the mixture was stirred at 100° C. for 10 min. Reduced iron (90%, 2.6 g) was added at room temperature, and the mixture was stirred at 100° C. for 3 hrs. After the completion of the reaction, the reaction mixture was filtered (celite), and the filtrate was concentrated under reduced pressure. Water was added to the residue and the mixture was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate:methylene chloride=2:1:1) to give the title compound (1.2 g) as a white solid.

Workup

  1. stirringthe mixture was stirred at 100° C. for 3 hrs
  2. customAfter the completion of the reaction
  3. filtrationthe reaction mixture was filtered (celite)
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater was added to the residue
  6. additionthe mixture was diluted with ethyl acetate
  7. washwashed with water and saturated brine
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate:methylene chloride=2:1:1)

Sources & evidence

ORD record
ord-62f16a1e01cd4bfea4bb1a8aff1a5ac9
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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