HCID 58368656, compound → HCID 58368504, compound

HRID 1192698Notes

Reaction equation

HRID 1192698 reaction equation
[Cl:1][C:2]1[C:3](I)=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[Cu](C#N)[C:18]#[N:19]>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:18]#[N:19])=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 58368656HCID 58368656, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 58368504HCID 58368504, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl 5-chloro-2-hydroxy-4-iodo-3-nitrobenzoate (5.00 g, 14.0 mmol) and copper cyanide (1.9 g, 21 mmol) in N,N-dimethylformamide (25 mL) was heated at 110° C. for 2 hours. After cooling to room temperature, the mixture was quenched with 1 N HCl and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over magnesium sulfate and then evaporated to dryness under reduced pressure. The residue was used directly in the next step (3.6 g, 100%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was quenched with 1 N HCl
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-935547cf9e274b0bbef9cf6898d298b0
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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