2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Agomelatine

HRID 541491Notes

Reaction equation

HRID 541491 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH2:9][CH:10]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:5][CH:4]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 68283667HCID 68283667, compound

Product 1

HCID 82148AgomelatineYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound obtained in Step E (100 mg, 0.41 mmol) in dichloromethane (4 mL) there is added, at ambient temperature, DDQ (111 mg, 0.49 mmol). The reaction mixture is stirred for 2 days and then washed with saturated NaHCO3 solution. The aqueous phase is extracted with ethyl acetate, and the organic phases are collected and then dried using brine and then over MgSO4. After filtration, the solvents are evaporated off under reduced pressure and the crude reaction mixture obtained is purified by chromatography on a silica column (eluant: ethyl acetate/petroleum ether 90/10, then ethyl acetate/methanol 90/10) to yield the title product in a yield of 48%.

Workup

  1. washwashed with saturated NaHCO3 solution
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. customthe organic phases are collected
  4. customdried
  5. filtrationAfter filtration
  6. customthe solvents are evaporated off under reduced pressure
  7. customthe crude reaction mixture
  8. customobtained
  9. customis purified by chromatography on a silica column (eluant

Sources & evidence

ORD record
ord-9cf1f94d8b8c4715a5a6ee9b7622d8d4
Source dataset
uspto-grants-2014_10
Patent number
US08871975B2

Reaction notes

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