2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(3-chloropropyl)-5-methyl-1H-quinolin-2-one

HRID 2103208Notes

Reaction equation

HRID 2103208 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH3:15])[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:16].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.O1CCOCC1>CCOC(C)=O>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH3:15])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]1=[O:16]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 312751,4-DioxaneHCID 190277331-(3-Chloropropyl)-5-methyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 179560681-(3-chloropropyl)-5-methyl-1H-quinolin-2-oneYield 66.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A microwave vial was charged with 1-(3-chloropropyl)-5-methyl-3,4-dihydro-1H-quinolin-2-one (0.081 g, 0.34 mmol), DDQ (0.116 g, 0.51 mmol), dioxane (2 mL) and sealed. After microwave irradiation, 175° C., 10 min, the reaction was diluted with EtOAc (50 mL), washed with sat aqueous NaHCO3 (2×15 mL) and the organic phase was dried (Na2SO4), filtered, concentrated under reduced pressure and the residue was purified with prep RP-HPLC to yield the crude title compound (0.053 g), which was used without further purification. HPLC-MS (ammonium acetate) [M+H]+=236.2.

Workup

  1. customsealed
  2. customAfter microwave irradiation, 175° C., 10 min
  3. washwashed
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified with prep RP-HPLC

Sources & evidence

ORD record
ord-508734674cb8455ca6ab9a31f97dd1af
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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