1-Chloro-4-nitrobenzene → HCID 67148374, compound

HRID 2425857Notes

Reaction equation

HRID 2425857 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.Cl[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.CC(C)([O-])C.[K+].[Cl-].[NH4+]>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 4

HCID 74741-Chloro-4-nitrobenzeneHCID 23393Picolyl chlorideHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 67148374HCID 67148374, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

8.66 g of 4-chloronitrobenzene and 8.2 g of 2-chloromethylpyridine in solution in 100 ml of dimethyl sulfoxide are slowly added to 22.44 g of potassium tert-butoxide in 500 ml of dimethyl sulfoxide. After 18 hours at room temperature, the mixture is hydrolyzed with a saturated ammonium chloride solution and extracted three times with dichloromethane. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is filtered on silica H (eluent dichloromethane) in order to obtain 10.695 g of the expected product.

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. filtrationThe residue is filtered on silica H (eluent dichloromethane) in order

Sources & evidence

ORD record
ord-19e57cde99194bbe8963eb4fac64a5f0
Source dataset
uspto-grants-2011_06
Patent number
US07968534B2

Reaction notes

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