Acetic Acid → 1-amino-5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

HRID 1927140Notes

Reaction equation

HRID 1927140 reaction equation
[N+:1]([C:4]1[S:5][CH:6]=[C:7]2[C:11](=[O:12])[N:10]([CH:13]3[CH2:18][CH2:17][C:16](=[O:19])[NH:15][C:14]3=[O:20])[C:9](=[O:21])[C:8]=12)([O-])=O.C(O)(=O)C>C(O)C.O.[Fe]>[NH2:1][C:4]1[S:5][CH:6]=[C:7]2[C:11](=[O:12])[N:10]([CH:13]3[CH2:18][CH2:17][C:16](=[O:19])[NH:15][C:14]3=[O:20])[C:9](=[O:21])[C:8]=12

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 59765270HCID 59765270, compound

Product 1

HCID 597652711-amino-5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dioneYield 34%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.309 g of 1-nitryl-5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione was suspended in 20 mL of ethanol and 20 mL of water, and 0.7 g freshly-activated iron powder (washed with water after hydrochloric acid treatment) and 5 mL acetic acid were added and refluxed for 2 h. The reaction mixture was cooled and filtered. The filtered solution was evaporated to dryness; and the remaining residue was dissolved in 150 mL of ethyl acetate, washed with 40 mL of water and 40 mL of brine, dried over anhydrous MgSO4, filtered, and evaporated to dryness. The remaining residue was purified on silica gel column chromatography to obtain a solid (0.095 g).

Workup

  1. temperaturerefluxed for 2 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customThe filtered solution was evaporated to dryness
  5. dissolutionand the remaining residue was dissolved in 150 mL of ethyl acetate
  6. washwashed with 40 mL of water and 40 mL of brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe remaining residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-a3a2282e6f25477393e4b28b9ffcfdb0
Source dataset
uspto-grants-2012_05
Patent number
US08183260B2

Reaction notes

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