4-Fluoroaniline → HCID 59256555, compound

HRID 640799Notes

Reaction equation

HRID 640799 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[C:17]([C:18]([OH:20])=O)=[C:16]([N+:24]([O-:26])=[O:25])[C:15]=1[OH:27].[F:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1>C1COCC1.CN(C=O)C>[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[C:17]([C:18]([NH:33][C:32]2[CH:34]=[CH:35][C:29]([F:28])=[CH:30][CH:31]=2)=[O:20])=[C:16]([N+:24]([O-:26])=[O:25])[C:15]=1[OH:27]

Participants

6

Reactant 3

HCID 97314-FluoroanilineHCID 682631,1'-CarbonyldiimidazoleHCID 106584324,6-dichloro-3-hydroxy-2-nitrobenzoic acid

Product 1

HCID 59256555HCID 59256555, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

CDI (2.2 g, 0.013 mol) was added to a stirred solution of 4,6-dichloro-3-hydroxy-2-nitrobenzoic acid (3.0 g, 0.012 mol) in anhydrous THF (30 mL) and DMF (2 mL). After 40 min, 4-fluoroaniline (4 mL, 0.042 mol) was added. The solution was heated under reflux overnight, cooled, and concentrated to a dark brown viscous oil. The oil was purified via SiO2-gel chromatography (dichloromethane/methanol, 19:1-9:1) to yield 4,6-dichloro-N-(4-fluorophenyl)-3-hydroxy-2-nitrobenzamide as a light brown oil (2.7 g, 65%).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. concentrationconcentrated to a dark brown viscous oil
  5. customThe oil was purified via SiO2-gel chromatography (dichloromethane/methanol, 19:1-9:1)

Sources & evidence

ORD record
ord-aaa02d2e6c8d41449917522312ade0a1
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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