1,2-Dichloro-4-nitrobenzene → HCID 66233216, compound

HRID 1361472Notes

Reaction equation

HRID 1361472 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[Cl:11].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[N:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O>[Cl-].[Na+].O.C(OCC)(=O)C>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[Cl:11])=[N:17][CH:18]=1

Participants

7

Reactant 4

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 1785160645-chloropyridin-2-ol

Product 1

HCID 66233216HCID 66233216, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

1,2-Dichloro-4-nitrobenzene (19.2 g), 12.9 g of 5-chloropyridine-2-ol, and 10.4 g of potassium carbonate were added to 50 mL of dimethylacetamide, and the mixture was allowed to react at 90 to 110° C. for 15 hr. The reaction mixture was cooled, ethyl acetate and brine were then added thereto, followed by separation and washing with brine. The ethyl acetate layer was concentrated, and the precipitated crystals were collected by filtration. The filtrate was concentrated, and the crude product thus obtained was purified by column chromatography on silica gel (BW300, manufactured by Fuji Sylysia Chemical Ltd., solvent: n-hexane/ethyl acetate) to give 15.75 g of 5-chloro-2-(2-chloro-4-nitrophenoxy)pyridine (yield 55.2%).

Workup

  1. customto react at 90 to 110° C. for 15 hr
  2. temperatureThe reaction mixture was cooled
  3. customfollowed by separation
  4. washwashing with brine
  5. concentrationThe ethyl acetate layer was concentrated
  6. filtrationthe precipitated crystals were collected by filtration
  7. concentrationThe filtrate was concentrated
  8. customthe crude product thus obtained
  9. customwas purified by column chromatography on silica gel (BW300, manufactured by Fuji Sylysia Chemical Ltd., solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-414a903699174fccb758517055c1f923
Source dataset
uspto-grants-2011_02
Patent number
US07880006B2

Reaction notes

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