Nitrobenzene → HCID 58020106, compound

HRID 1632114Notes

Reaction equation

HRID 1632114 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[Al+3].[Cl-].[Cl-].[Cl-].[O:14]1[C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=[N:15]1.[C:22]([O:25][CH2:26][CH3:27])(=O)C>>[OH:14][C:18]1[C:17]([C:19]([C:18]2[O:14][N:15]=[CH:16][CH:17]=2)=[O:20])=[CH:16][CH:27]=[C:26]([O:25][CH3:22])[C:19]=1[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 4

HCID 7416NitrobenzeneHCID 8857Ethyl AcetateHCID 2736707Isoxazole-5-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 58020106HCID 58020106, compoundYield 32%

Procedure

Nitrobenzene (1 mL) and AlCl3 (154 mg, 1.15 mmol) were placed in an 8 mL vial with a stir bar and stirred at room temperature for 10 min. Isoxazole-5-carbonyl chloride (151 mg, 1.15 mmol) was added and the solution was allowed to stir at room temperature for another 30 minutes. Then adding I-81 (250 mg, 0.96 mmol) was added and the resulting solution was stirred at room temperature for 20 hours and heating for 1 hour. The reaction mixture was diluted with ethyl acetate (90 mL) washed with water, brine and dried over Na2SO4. After filtration and removal of solvent, the residue was purified by silica gel column chromatography with ethyl acetate/hexane to yield 100 mg (32%) of P-129. 1H NMR (400 MHz, CDCl3) 3.91 (s, 3H) 6.71-6.78 (m, 1H) 7.10-7.15 (m, 1H) 7.52-7.64 (m, 1H) 7.57-7.64 (m, 1H), 7.72-7.77 (m, 1H) 8.21-8.30 (m, 1H) 8.44-8.47 (m, 1H), 8.48-8.53 (m, 1H), 12.62 (s, 1H) ppm.

Workup

  1. stirringto stir at room temperature for another 30 minutes
  2. additionThen adding I-81 (250 mg, 0.96 mmol)
  3. additionwas added
  4. stirringthe resulting solution was stirred at room temperature for 20 hours
  5. temperatureheating for 1 hour
  6. washwashed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration and removal of solvent
  9. customthe residue was purified by silica gel column chromatography with ethyl acetate/hexane

Sources & evidence

ORD record
ord-6d4365f6bcaa4ea6a12753c49e79b293
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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