Acetic Anhydride → HCID 9863739, compound

HRID 2084987Notes

Reaction equation

HRID 2084987 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12](=[O:26])[NH:13][C:14](=[O:25])[C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:27](OC(=O)C)(=[O:29])[CH3:28].C(=O)(O)[O-].[Na+]>C(O)C.ClCCl.[Pd]>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12](=[O:26])[NH:13][C:14](=[O:25])[C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:27](=[O:29])[CH3:28])[CH:17]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 22728653HCID 22728653, compound

Product 1

HCID 9863739HCID 9863739, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-(Indan-5-ylamino)-4-(3-nitrophenyl)-1H-pyrrole-2,5-dione (Table A, Example A359; 0.3 g, 0.9 mmol) and 10% Pd/C (60 mg) in ethanol (25 mL) was hydrogenated at atmospheric temperature and pressure for 2 hours. The reaction mixture was filtered through Kieselguhr and the filtrate concentrated in vacuo to give an orange solid. The crude product was taken up in dichloromethane (5 mL) and treated with acetic anhydride (85 μL, 0.9 mmol) and stirred for 3 hours at ambient temperature. The reaction mixture was poured onto saturated aqueous sodium bicarbonate solution (10 mL) and extracted into ethyl acetate (3×10 mL). The combined organics were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Chromatography on silica gel using dichloromethane-methanol gave the desired compound as an orange powder.

Workup

  1. customwas hydrogenated at atmospheric temperature and pressure for 2 hours
  2. filtrationThe reaction mixture was filtered through Kieselguhr
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give an orange solid
  5. extractionextracted into ethyl acetate (3×10 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56c8e190c1f6403abc0bb0ed53f5dc2f
Source dataset
uspto-grants-2004_04
Patent number
US06719520B2

Reaction notes

Loading…