Hydroquinone → HCID 71735927, compound

HRID 1053574Notes

Reaction equation

HRID 1053574 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]([CH3:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[C:19]1([CH:26]=[CH:25][C:23]([OH:24])=[CH:22][CH:21]=1)[OH:20]>CN(C=O)C>[CH3:12][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][CH2:3][CH2:2][O:20][C:19]1[CH:26]=[CH:25][C:23]([OH:24])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 61288549N-(3-bromopropyl)-N-methylaniline

Product 1

HCID 71735927HCID 71735927, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 9a (500 mg, 2.7 mmol), K2CO3 (740 mg, 5.4 mmol), and KI (445 mg, 2.7 mmol) in DMF (50 mL) was bubbled with argon for 10 min Hydroquinone (589 mg, 5.4 mmol) was added to the mixture under argon. The reaction mixture was heated and stirred at 80° C. for 6 hours. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 100 mLs water. The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with CH2Cl2 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 silica gel column chromatography with hexane/EtOAc to provide the compound 9 (170 mg, 0.66 mmol, 24% yield) as a white solid. HRMS (ESI, positive) m/z calcd. for C16H20NO2 [M+H]+: 258.14886, found: 258.14888. 1H NMR (400 MHz, Chloroform-d) δ 7.36-7.27 (m, 2H), 6.94-6.70 (m, 7H), 5.94 (broad s, 1H), 4.00 (t, J=5.9 Hz, 2H), 3.60 (t, J=7.0 Hz, 2H), 3.01 (s, 3H), 2.09 (p, J=6.2 Hz, 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 mLs water
  6. extractionThe mixture was then extracted with CH2Cl2
  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 silica gel column chromatography with hexane/EtOAc

Sources & evidence

ORD record
ord-3ed6e073011b4103a6d62e36e81689fa
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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