HCID 869878, compound → HCID 11821097, compound

HRID 1609584Notes

Reaction equation

HRID 1609584 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:7]2=[O:21])([O-])=O>Cl>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:7]2=[O:21]

Participants

3

Reactant 1

HCID 869878HCID 869878, compound

Product 1

HCID 11821097HCID 11821097, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 200 ml of conc. hydrochloric acid was added 21.1 g of stannous chloride under ice cooling, and 9.0 g of 5-nitro-2-(3-pyridylmethyl)-1H-isoindole-1,3 (2H)-dione was added. The reaction mixture was stirred at room temperature for 15 minutes and stirred at 80° C. for 30 minutes. After cooling, the mixture was filtered, and the resultant solid was mixed with water and made alkaline with aqueous ammonia. To this mixture was added 500 ml of tetrahydrofuran, and the resultant mixture was filtered with celite. The filtrate was shaken with methylene chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was chromatographed on a column of silica gel, eluting with ethyl acetate and hexane (2:1) to give 7.4 g of the titled compound.

Workup

  1. stirringstirred at 80° C. for 30 minutes
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. additionthe resultant solid was mixed with water
  5. additionTo this mixture was added 500 ml of tetrahydrofuran
  6. filtrationthe resultant mixture was filtered with celite
  7. stirringThe filtrate was shaken with methylene chloride
  8. washThe organic layer was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe resultant residue was chromatographed on a column of silica gel
  12. washeluting with ethyl acetate and hexane (2:1)

Sources & evidence

ORD record
ord-05ad165aa8d64a6cb39bc139dabed9bb
Source dataset
uspto-grants-1995_03
Patent number
US05401756

Reaction notes

Loading…