p-Fluoronitrobenzene → HCID 59285822, compound

HRID 1011591Notes

Reaction equation

HRID 1011591 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3].[H-].[Na+].F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.[Cl-].[NH4+]>CN(C)C=O.O>[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=3)[CH:14]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3]

Participants

7

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59285873HCID 59285873, compound

Product 1

HCID 59285822HCID 59285822, compoundYield 8.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Under ice-cooling, a solution of 2-aminocarbonylamino-5-(3-hydroxyphenyl)pyrrole-3-carboxamide (Compound No. 3-2, 100 mg, 0.38 mmol) in N,N-dimethylformamide (1.5 mL) was added to a suspension of 60% sodium hydride (23 mg, 0.58 mmol) in N,N-dimethylformamide (1.5 mL) and the mixture was stirred for 35 minutes. Moreover, 4-fluoronitrobenzene (61 μL, 0.57 mmol) was added thereto and the whole was stirred overnight at 50° C. Saturated aqueous ammonium chloride solution (3 mL) and water (3 mL) were added to the reaction solution, extracted with ethyl acetate (10 mL). The organic layer was washed with brine (10 mL) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give the target compound (12 mg) as a yellow solid (Yield 8%).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe whole was stirred overnight at 50° C
  3. extractionextracted with ethyl acetate (10 mL)
  4. washThe organic layer was washed with brine (10 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-94a6fa9cbfa44709b210076d83165e77
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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