Hydrochloric Acid → HCID 20288695, compound

HRID 607260Notes

Reaction equation

HRID 607260 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[OH-].[K+].Cl[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=1[N+:20]([O-:22])=[O:21].Cl>CS(C)=O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[N+:20]([O-:22])=[O:21])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 14797Potassium Hydroxide

Product 1

HCID 20288695HCID 20288695, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of hydroquinone (1.21 g, 0.011 mol) and potassium hydroxide (0.894 g, 0.0159 mol) in anhydrous dimethylsulfoxide (8 mL) was heated at 90° C. for 30 minutes under a nitrogen atmosphere. A solution of 4-chloro-3-nitrobenzonitrile (1.806 g, 0.0099 mol) in dimethylsulfoxide (8 mL) was added dropwise over a 30 minute period at 90°, then let the reaction stir for 1 hour at the same temperature. The reaction was then cooled in an ice bath and poured into 30 mL of ice-water. The mixture was acidified with concentrated hydrochloric acid to pH 3 and extracted with ethyl ether (3×100 mL). The combined ethereal extracts were washed with water (3×150 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation under vacuum. Purification by silica gel chromatography using 4% ethyl acetate/methylene chloride as eluent provided the product as an orange solid (0.984 g, 39%).

Workup

  1. temperatureThe reaction was then cooled in an ice bath
  2. extractionextracted with ethyl ether (3×100 mL)
  3. washThe combined ethereal extracts were washed with water (3×150 mL) and brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation under vacuum
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-e716ba95d4744e9a9b368d8c0633b3ae
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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