Hydroquinone → HCID 21335871, compound

HRID 1053553Notes

Reaction equation

HRID 1053553 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].[C:18]1([CH:25]=[CH:24][C:22]([OH:23])=[CH:21][CH:20]=1)[OH:19]>CN(C=O)C>[OH:19][C:18]1[CH:25]=[CH:24][C:22]([O:23][CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:4])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 11485Chloroacetanilide

Product 1

HCID 21335871HCID 21335871, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 1a (338 mg, 2 mmol), K2CO3 (553 mg, 4 mmol), and KI (66 mg, 0.4 mmol) in DMF (50 mL) was bubbled with argon for 10 min Hydroquinone (440 mg, 4 mmol) was added to the mixture under argon. The reaction mixture was heated and stirred at 80° C. for 6 hr. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 100 mL water. The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with EtOAc and the combined organic layer was washed with water and then brine and was dried over Na2SO4. The solvent was evaporated and the residue was purified by flash chromatography on silica gel to provide the compound (150 mg, 0.62 mmol, 31% yield) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.32 (br s, 1H), 7.60 (d, J=7.6 Hz, 2H), 7.38 (t, J=7.8 Hz, 2H), 7.18 (t, J=7.4 Hz, 1H), 6.90 (d, J=9.2 Hz, 2H), 6.84 (d, J=9.2 Hz, 2H), 5.07 (br s, 1H), 4.58 (s, 2H).

Workup

  1. additionwas added to the mixture under argon
  2. temperatureThe reaction mixture was heated
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was evaporated
  5. customthe residue was quenched with 100 mL water
  6. extractionThe mixture was then extracted with EtOAc
  7. washthe combined organic layer was washed with water
  8. dry with materialbrine and was dried over Na2SO4
  9. customThe solvent was evaporated
  10. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-2609d90403284c8fb034fd53a656a45d
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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