Acetic Acid → HCID 59354866, compound

HRID 655476Notes

Reaction equation

HRID 655476 reaction equation
[CH3:1][C:2]1([CH3:35])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)=[CH:10][CH:9]=2)=[C:4]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=2)[O:3]1.CC(O)=O>C(O)C.[Fe]>[NH2:32][C:29]1[CH:30]=[CH:31][C:26]([C:4]2[O:3][C:2]([CH3:1])([CH3:35])[C:6](=[O:7])[C:5]=2[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)=[CH:10][CH:9]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 593548082,2-dimethyl-5-(4-nitrophenyl)-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one

Product 1

HCID 59354866HCID 59354866, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 2,2-dimethyl-5-(4-nitrophenyl)-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one (0.6 g, 1.28 mmol) in ethanol (10 mL) was added AcOH (1.28 mL) at RT under N2 atmosphere. After being stirred for 10 min at RT, the reaction mixture was heated to 70° C. and Fe (0.524 g, 9.04 mmol) and FeCl3 (0.062 g, 0.38 mmol) were added under N2 atmosphere. The reaction mixture was stirred at 70° C. for 2 h. After completion of starting material (by TLC), reaction mixture was cooled to RT, and the volatiles were evaporated in vacuo to obtain the crude product. The crude product was extracted in EtOAc (25 mL), washed with water (2×10 mL), brine and dried over anhydrous Na2SO4. After filtration and evaporation, the crude material was purified by silica gel column chromatography to afford 5-(4-aminophenyl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one (400 mg, 71%), as a yellow solid.

Workup

  1. temperaturethe reaction mixture was heated to 70° C.
  2. stirringThe reaction mixture was stirred at 70° C. for 2 h
  3. customAfter completion of starting material (by TLC), reaction mixture
  4. temperaturewas cooled to RT
  5. customthe volatiles were evaporated in vacuo
  6. customto obtain the crude product
  7. extractionThe crude product was extracted in EtOAc (25 mL)
  8. washwashed with water (2×10 mL), brine
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationAfter filtration and evaporation
  11. customthe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a6d9936e81834a34b0046d4b8dafec17
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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