Water → 6-Fluoro-N-(2-fluorophenyl)-3-nitro-4-quinolinamine

HRID 1672314Notes

Reaction equation

HRID 1672314 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[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][CH:21]=[CH:20][C:18]=1[NH2:19].O>C(O)(=O)C>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([N+:13]([O-:15])=[O:14])=[C:2]2[NH:19][C:18]1[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=1[F:16]

Participants

5

Reactant 3

HCID 962WaterHCID 95842-FluoroanilineHCID 108231514-Chloro-6-fluoro-3-nitro-quinoline

Product 1

HCID 600469356-Fluoro-N-(2-fluorophenyl)-3-nitro-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.4 g (1.8 mmol) of 4-chloro-6-fluoro-3-nitro-quinoline (Example 19c) and 0.17 ml (1.98 mmol) 2-fluoroaniline in 5 ml acetic acid are stirred overnight at rt. Crystals are formed. The mixture is poured into water, the solid material is filtered off and washed with water. The residue is dissolved in CH2Cl2 and washed twice with water. The organic phase is dried over MgSO4 and most of the solvent is evaporated. The title compound is obtained from this solution as yellow crystals by adding hexane. The compound is filtered off, washed with hexane and dried (70° C., high-vacuum). mp: 161-162° C.; MS: 302 (M++1); HPLC: tret=10.24 min (Grad 1).

Workup

  1. customCrystals are formed
  2. filtrationthe solid material is filtered off
  3. washwashed with water
  4. dissolutionThe residue is dissolved in CH2Cl2
  5. washwashed twice with water
  6. dry with materialThe organic phase is dried over MgSO4 and most of the solvent
  7. customis evaporated

Sources & evidence

ORD record
ord-43ed0cb8373a4959ba02acdcfee46b7f
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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