2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 59467517, compound

HRID 1715675Notes

Reaction equation

HRID 1715675 reaction equation
[N:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[CH:5]=[N:6]2.C[Li].Cl[C:18]1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCCC1>[CH3:18][C:5]1[C:4]2[CH:11]=[CH:12][CH:13]=[CH:14][C:3]=2[C:2]2[C:7](=[CH:8][CH:9]=[CH:10][N:1]=2)[N:6]=1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 12342817Benzo[c][1,5]naphthyridineHCID 178418348HCID 178418348, compound

Product 1

HCID 59467517HCID 59467517, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.0 g benzo[c][1,5]naphthyridine (5.5 mmol) was dissolved in 30 mL tetrahydrofuran (THF) and then cooled to −78° C. under nitrogen with stirring. 4.4 mL methyl lithium (MeLi) (6.6 mmol, 1.5M) was added and reacted for 1 hr. After quenching the reaction by a saturated ammonium chloride (NH4Cl) solution, extraction by ethyl acetate, drying, and concentration, 30 mL THF and 1.87 g 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (8.2 mmol) were added and reacted for 8 hr. After extraction by ethyl acetate, drying, concentration, and purification by silicon-gel column, 0.83 g light yellow solid was obtained, with a yield of 77%.

Workup

  1. customreacted for 1 hr
  2. customAfter quenching
  3. customthe reaction
  4. extractionby a saturated ammonium chloride (NH4Cl) solution, extraction by ethyl acetate
  5. customdrying
  6. additionwere added
  7. customreacted for 8 hr
  8. extractionAfter extraction by ethyl acetate
  9. customdrying
  10. concentrationconcentration, and purification by silicon-gel column

Sources & evidence

ORD record
ord-69daf9b845984f5eb53957e5afc5b9dd
Source dataset
uspto-grants-2010_09
Patent number
US07799918B2

Reaction notes

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