Sodium Iodide → HCID 22227049, compound

HRID 1745906Notes

Reaction equation

HRID 1745906 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C([O-])([O-])=O.[Cs+].[Cs+].[I-].[Na+].Cl.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]Cl>O.CN(C=O)C>[N+:9]([C:3]1[CH:4]=[C:5]([O:8][CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)[CH:6]=[CH:7][C:2]=1[NH2:1])([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 23392Picolyl chloride hydrochlorideHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 22227049HCID 22227049, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Amino-3-nitrophenol (5.00 g, 32.4 mMol), Cs2CO3 (22.8 g, 70 mMol), sodium iodide (476 mg, 3.20 mMol) and 2-picolyl chloride hydrochloride (11.2 g, 35 mMol) were added to 20 mL of anhydrous DMF under an atmosphere of dry N2. The reaction mixture was stirred overnight at ambient temperature. The reaction mixture is then poured into water. The precipitate was collected via suction filtration. The precipitate was partitioned between DCM and 1.0 N aqueous NaOH. The organic layer was washed 2 more times with 1 N aqueous NaOH to remove any unreacted phenol. The organic layer was then washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give 7.7 g of a dark red solid. The solid was chromatographed on flash silica gel eluting with EtOAc/DCM (2080) to give 3.7 g of the title compound 47A as an orange solid.

Workup

  1. filtrationThe precipitate was collected via suction filtration
  2. customThe precipitate was partitioned between DCM and 1.0 N aqueous NaOH
  3. washThe organic layer was washed 2 more times with 1 N aqueous NaOH
  4. customto remove any unreacted phenol
  5. washThe organic layer was then washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3ebdf901aa4044b38297fd39c0c5b3c8
Source dataset
uspto-grants-2006_03
Patent number
US07019147B1

Reaction notes

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