1-Fluoro-3-nitrobenzene → HCID 16128758, compound

HRID 547592Notes

Reaction equation

HRID 547592 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][NH:8][CH:9]=1)=[O:4].[H-].[Na+].F[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1>CO>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 98231-Fluoro-3-nitrobenzeneHCID 24758Sodium hydrideHCID 178418785HCID 178418785, compound

Product 1

HCID 16128758HCID 16128758, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

1H-Imidazole-4-carboxylic acid methyl ester (1 g, 7.9 mmol) was dissolved in MeOH and NaH (348 mg, 8.7 mmol) was added slowly. When the gas evolution had ceased 1-fluoro-3-nitro benzene (926 uL, 8.7 mmol) was added, and the mixture was heated to 150° C. under N2 for 16 h. After cooling to room temperature the precipitation was isolated by suction filtration, washed with MeOH, and dried under vacuum to afford 1.3 g (67%) of 20. HRMS (ESI+): m/z=247.2091 [M+H]

Workup

  1. additionwas added
  2. temperatureAfter cooling to room temperature
  3. customthe precipitation
  4. customwas isolated by suction filtration
  5. washwashed with MeOH
  6. customdried under vacuum

Sources & evidence

ORD record
ord-80783d87769b4c498bde4df2a8617965
Source dataset
uspto-grants-2011_05
Patent number
US07939556B2

Reaction notes

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