HCID 18705862, compound → HCID 18705870, compound

HRID 2287848Notes

Reaction equation

HRID 2287848 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH:5]1[CH2:18][C:8]2=[CH:9][C:10]3[C:11](=[O:17])[NH:12][C:13](=O)[C:14]=3[CH:15]=[C:7]2[CH2:6]1)[CH2:2][CH3:3]>CC(O)=O.CO.[Zn]>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:18][C:8]2=[CH:9][C:10]3[C:11](=[O:17])[NH:12][CH2:13][C:14]=3[CH:15]=[C:7]2[CH2:6]1)[CH2:20][CH3:21]

Participants

5

Reactant 1

HCID 18705862HCID 18705862, compound

Product 1

HCID 18705870HCID 18705870, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
113 °C

Procedure

(Ref. Brewster, J. H.; Fusco A. M. J.Org. Chem., 28, 501-503 (1963)) A solution of 6-(dipropylamino)-6,7-dihydrocyclopent[f]isoindole-1,3(2H,5H)-dione 93 (0.45 g, 1.6 mmol) in glacial HOAc (50 mL) was treated with Zinc dust (1.05 g, 16.0 mmol) then refluxed at 113° C. for 24 h. The reaction was cooled to r.t., diluted with MeOH and filtered through a pad of celite. The filtrate was concentrated and the residue was diluted with H2O, basified with sat'd Na2CO3, and extracted with CH2Cl2. The organic layers were washed with brine, dried (MgSO4), and concentrated. The resulting solid was purified using silica gel, eluting with 2:1 heptane/acetone to give 94 as a white solid (m.p. 206-208° C.).

Workup

  1. temperatureThe reaction was cooled to r.t.
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated
  4. additionthe residue was diluted with H2O
  5. extractionextracted with CH2Cl2
  6. washThe organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe resulting solid was purified
  10. washeluting with 2:1 heptane/acetone

Sources & evidence

ORD record
ord-f77d648a5a0e45d090ef530a6e71376c
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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