Acetic Acid → HCID 131721162, compound

HRID 1418298Notes

Reaction equation

HRID 1418298 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([N:15]2[C:23](=[O:24])[C:18]3=[CH:19][CH2:20][CH2:21][CH2:22][N:17]3[C:16]2=[O:25])=[C:8]([F:26])[CH:7]=1>C(OCC)(=O)C>[NH2:12][C:11]1[C:6]([Cl:5])=[CH:7][C:8]([F:26])=[C:9]([N:15]2[C:23](=[O:24])[C:18]3=[CH:19][CH2:20][CH2:21][CH2:22][N:17]3[C:16]2=[O:25])[CH:10]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 131721163HCID 131721163, compound

Product 1

HCID 131721162HCID 131721162, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

After an acetic acid (172 mL) solution of reduced iron (21.0 g) was stirred for one hour under reflux, an ethyl acetate (113 mL) solution of 2-(4-chloro-2-fluoro-5-nitrophenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (5.14 g, 0.016 mol) was dropwise added to the mixture at the same temperature. The reaction mixture was stirred for 2 hours under reflux and cooled down to room temperature. After filtration of the resulting mixture, 1N hydrochloric acid (250 mL) was added to the filtrate, and the organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL×2 times). The organic layer combined was washed with water (300 mL) and dried over anhydrous magnesium sulfate. After removal of magnesium sulfate by filtration, the filtrate was evaporated to give crude product, which was purified by silica gel column (Wakogel C-200, ethyl acetate/hexane =1/1) to obtain a white solid of 2-(5-amino-4-chloro-2-fluorophenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (2.81 g, yield:59.4%).

Workup

  1. temperatureunder reflux
  2. temperatureunder reflux
  3. filtrationAfter filtration of the resulting mixture, 1N hydrochloric acid (250 mL)
  4. additionwas added to the filtrate
  5. customthe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (100 mL×2 times)
  7. washThe organic layer combined was washed with water (300 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter removal of magnesium sulfate
  10. filtrationby filtration
  11. customthe filtrate was evaporated
  12. customto give crude product, which
  13. customwas purified by silica gel column (Wakogel C-200, ethyl acetate/hexane =1/1)

Sources & evidence

ORD record
ord-b1564e13403946c98503c169d1ef2635
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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