Hydroquinone → HCID 71736092, compound

HRID 1053597Notes

Reaction equation

HRID 1053597 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:18][CH2:19]Cl)[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:6]=1.[C:21]([O-:24])([O-])=O.[K+].[K+].[C:27]1([CH:34]=[CH:33][C:31]([OH:32])=[CH:30][CH:29]=1)[OH:28]>CN(C=O)C>[OH:28][C:27]1[CH:34]=[CH:33][C:31]([O:32][CH2:2][CH2:3][N:4]([CH2:18][CH2:19][O:28][C:27]2[CH:34]=[CH:33][C:21]([OH:24])=[CH:30][CH:29]=2)[C:5]2[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:6]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 20702730Methyl 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate

Product 1

HCID 71736092HCID 71736092, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 27a (470 mg, 1.48 mmol), K2CO3 (440 mg, 3 mmol), and KI (50 mg, 0.3 mmol) in DMF (50 mL) was bubbled with argon for 10 min. Hydroquinone (660 mg, 6 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, then brine, and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography to provide the compound 27 (150 mg, 0.32 mmol, 22% yield) as a brown oil. 1H NMR (CDCl3, 400 MHz) δ 7.05 (d, J=8.4 Hz, 2H), 6.67-6.81 (m, 9H), 5.58 (bs, 2H), 4.09 (t, J=6.4 Hz, 4H), 3.80 (t, J=6.0 Hz, 7H), 3.69 (s, 3H), 2.56 (t, J=7.2 Hz, 2H), 2.35 (t, J=7.2 Hz, 2H), 1.89-1.96 (m, 2H); HRMS (ESI, positive) m/z calcd. for C27H32NO6 [M+H]+: 466.2230, found: 466.2204.

Workup

  1. customwas bubbled with argon for 10 min
  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 dried over Na2SO4
  9. customThe solvent was evaporated
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9a867d01e6f24547a253ba875701f965
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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