Sodium Dithionite → 1-amino-5-(1-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione

HRID 38504Notes

Reaction equation

HRID 38504 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])[N:15]([CH3:20])[C:14]3=[O:21])[C:9](=[O:22])[C:8]=12)([O-])=O.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CC(C)=O.O>[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])[N:15]([CH3:20])[C:14]3=[O:21])[C:9](=[O:22])[C:8]=12

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 59765277HCID 59765277, compound

Product 1

HCID 597653111-amino-5-(1-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dioneYield 52.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

0.097 g of 1-nitro-5-(1-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione was dissolved in 10 mL of acetone; and a solution obtained by dissolving 0.239 g of Na2S2O4 in 10 mL of water was added. The reaction mixture was refluxed for 2 h, cooled, and 10 mL of water were added. The aqueous phase was extracted with ethyl acetate (3×30 mL), the organic phases were combined, washed with 40 mL of water and 40 mL of brine, dried over anhydrous MgSO4, filtered, and evaporated to dryness to remove the solvent. The remaining residue was purified on silica gel column chromatography to yield a solid (0.046 g). MS (m/z): 292 (M−1)+.

Workup

  1. customand a solution obtained
  2. additionwas added
  3. temperatureThe reaction mixture was refluxed for 2 h
  4. temperaturecooled
  5. extractionThe aqueous phase was extracted with ethyl acetate (3×30 mL)
  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. customto remove the solvent
  11. customThe remaining residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-2e584dcf72d04e389f2a178251e07977
Source dataset
uspto-grants-2013_09
Patent number
US08524742B2

Reaction notes

Loading…