2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 90417406, compound

HRID 513950Notes

Reaction equation

HRID 513950 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH:12]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 90416764Ethyl 2-(7-((3-chlorobenzyl)oxy)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate

Product 1

HCID 90417406HCID 90417406, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 2-(7-((3-chlorobenzyl)oxy)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate (50.3 g, 134.5 mmol) in chloroform (905.2 mL) was added 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile (36.65 g, 161.4 mmol). The reaction was poured into 500 mL sat (aq) NaHCO3 and stirred for 15 min. To the resulting slurry was added diatomaceous earth (CELITE®) and the mixture was filtered over CELITE®. The phases were separated and the subsequent CELITE® washes, chloroform (2×400 mL), were used to extract the aqueous layer. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford a brown/red solid. The solid was triturated in 2-propanol (700 mL) and filtered to furnish the title compound (31.4 g, 55%). 1H NMR (400 MHz, DMSO-d6) δ 11.73 (s, 1H), 11.91-11.57 (m, 1H), 7.77 (s, 1H), 7.55 (s, 2H), 7.43 (t, J=4.8 Hz, 3H), 6.87 (s, 2H), 5.17 (s, 2H), 4.06 (d, J=7.0 Hz, 2H), 3.48 (s, 2H), 1.17 (t, J=7.2 Hz, 3H). [M+H]=372.1.

Workup

  1. additionThe reaction was poured into 500 mL
  2. additionTo the resulting slurry was added diatomaceous earth (CELITE®)
  3. filtrationthe mixture was filtered over CELITE®
  4. customThe phases were separated
  5. extractionto extract the aqueous layer
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto afford a brown/red solid
  9. customThe solid was triturated in 2-propanol (700 mL)
  10. filtrationfiltered

Sources & evidence

ORD record
ord-4389711936014018b2b2e2b05447a50d
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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