Hydrochloric Acid → HCID 21248421, compound

HRID 620033Notes

Reaction equation

HRID 620033 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.C(=O)([O-])[O-].[K+].[K+].Br[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1.Cl>[Fe].O.C(O)C>[F:24][C:20]1[CH:19]=[C:18]([NH:1][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[NH2:6])[CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 69462-NitroanilineHCID 11430Potassium CarbonateHCID 140821-Bromo-3-fluorobenzene

Product 1

HCID 21248421HCID 21248421, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

o-nitroaniline (2.8 g, 20.3 mmol), potassium carbonate (0.9 g, 6.5 mmol), cuprous iodide (0.78 g, 4.1 mmol) and 1-bromo-3-fluorobenzene (15.4 g, 88.0 mmol) were refluxed for 24 hours at 165° C. The reactant was subjected to steam distillation and the remainder was extracted with ethyl acetate. The ethyl acetate layer was washed, dried and concentrated in vacuo. The obtained residue was refined by a silica gel column chromatography (CHCl3). The eluent (1.2 g, 5.2 mmol) was refluxed for 1 hour together with powdered iron (2.9 g, 52 mmol), ethanol (4.2 ml), water (1 ml) and concd. hydrochloric acid (0.05 ml, 50 mmol), then the resultant was concentrated in vacuo.

Workup

  1. distillationThe reactant was subjected to steam distillation
  2. extractionthe remainder was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e774ade276aa4a0f8a26ee726beba477
Source dataset
uspto-grants-1989_04
Patent number
US04818761

Reaction notes

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