4-Fluoroaniline → HCID 60046932, compound

HRID 1672309Notes

Reaction equation

HRID 1672309 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>O>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:21][C:20]3[CH:22]=[CH:23][C:17]([F:16])=[CH:18][CH:19]=3)=[C:3]([N+:13]([O-:15])=[O:14])[CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 534398754,7-Dichloro-3-nitroquinoline

Product 1

HCID 60046932HCID 60046932, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.3 g (5.3 mmol) 4,7-dichloro-3-nitro-quinoline (Example 15b) and 0.525 g (5.3 mmol) 4-fluoroaniline are stirred at rt for 1 h. The reaction mixture is poured into 150 ml of water, and the resulting crystals are filtered off. After washing with water, the solid is dissolved in ca. 170 ml of ethanol and then concentrated to ca. 30 ml. The solution is cooled in ice-water. The crystals which precipitate are filtered off and dried overnight at 70° C. (high vacuum). mp: 198-200° C.; MS: 318 (M++1); HPLC: tret=10.92 min (Grad 1).

Workup

  1. filtrationthe resulting crystals are filtered off
  2. washAfter washing with water
  3. dissolutionthe solid is dissolved in ca. 170 ml of ethanol
  4. concentrationconcentrated to ca. 30 ml
  5. temperatureThe solution is cooled in ice-water
  6. filtrationThe crystals which precipitate are filtered off
  7. customdried overnight at 70° C. (high vacuum)
  8. customtret=10.92 min (Grad 1)

Sources & evidence

ORD record
ord-ace51838c99e490f8f2c6e54d9902c88
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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