HCID 15407842, compound → HCID 15407843, compound

HRID 2393511Notes

Reaction equation

HRID 2393511 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:19]=[CH:18][CH:17]=[CH:16][C:5]2=[C:6]2[C:15]=1[O:14][C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[O:7]2>C(O)(=O)C.CO.[Zn]>[CH:16]1[C:5]2=[C:6]3[C:15](=[CH:2][N:3]=[C:4]2[CH:19]=[CH:18][CH:17]=1)[O:14][C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[O:7]3

Participants

5

Reactant 1

HCID 15407842HCID 15407842, compound

Product 1

HCID 15407843HCID 15407843, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Under an inert atmosphere, 1 mmol of 6-chloro-5-aza-7,12-dioxabenz[a]anthracene and 8 mmol of powdered zinc are brought to 50° C. in 5 ml of acetic acid for 8 hours. After cooling, the reaction mixture is diluted in methanol and then filtered through Celite. The residue is concentrated under vacuum, then washed with saturated sodium hydrogen carbonate solution and then extracted with chloroform. The organic phase is dried over magnesium sulfate and concentrated under vacuum. The crude mixture is chromatographed by flash chromatography on silica gel (eluent: ethyl acetate/petroleum ether).

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered through Celite
  3. concentrationThe residue is concentrated under vacuum
  4. washwashed with saturated sodium hydrogen carbonate solution
  5. extractionextracted with chloroform
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe crude mixture is chromatographed by flash chromatography on silica gel (eluent: ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-a566e3b03a264807a28384a1d061dc23
Source dataset
uspto-grants-1998_09
Patent number
US05807882

Reaction notes

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