2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178475467, compound

HRID 55849Notes

Reaction equation

HRID 55849 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[NH:11][C:10](=[O:16])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[N:11]=[C:10]([OH:16])[CH:9]=[CH:8]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 99911448-Fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl acetate

Product 1

HCID 178475467HCID 178475467, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 8-fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl acetate (718 mg) in toluene (8 mL) was added DDQ (1.2 g). The resultant solution was heated at 70° C. over 48 h. After aqueous work-up with EtOAc, the crude product was purified by a flash silica column chromatography to afford the pure product (550 mg) as a colorless solid.

Workup

  1. customAfter aqueous work-up with EtOAc, the crude product was purified by a flash silica column chromatography

Sources & evidence

ORD record
ord-5385420a43ac473caac5d976331e09a0
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Reaction notes

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