Water → 3-Chloro-5-fluoro-4-(quinolin-3-yloxy)phenylamine

HRID 1370484Notes

Reaction equation

HRID 1370484 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:20]([O-])=O)[CH:5]=[C:6]([F:19])[C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.[NH4+].[Cl-].O>CCO.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:20])[CH:5]=[C:6]([F:19])[C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 221487343-Chloro-5-fluoro-4-(quinolin-3-yloxy)nitrobenzene

Product 1

HCID 221488123-Chloro-5-fluoro-4-(quinolin-3-yloxy)phenylamineYield 47.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-chloro-5-fluoro-4-(quinolin-3-yloxy)nitrobenzene (50.1) (0.980 g) and NH4Cl (1.64 g) in EtOH(50 mL)—H2O (5 mL), was added iron powder (1.92 g). The mixture was heated to reflux for 1 h. After cooling the reaction mixture was filtered through short celite pad. The filtrate was concentrated, diluted with sat.NaHCO3 and extracted with AcOEt (30 mL×3). The combined organic layers were washed with brine and dried over Na2SO4. Concentration of solvent afford crude product, which was purified by column chromatography (silica gel, AcOEt:hexane=1:3) to provide aniline 50.2 (0.420 g) as a colorless solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. temperatureAfter cooling the reaction mixture
  4. filtrationwas filtered through short celite pad
  5. concentrationThe filtrate was concentrated
  6. additiondiluted
  7. extractionNaHCO3 and extracted with AcOEt (30 mL×3)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over Na2SO4
  10. customConcentration of solvent afford crude product, which
  11. customwas purified by column chromatography (silica gel, AcOEt:hexane=1:3)

Sources & evidence

ORD record
ord-b91882584b0646b89e1b79c8b8bf1b84
Source dataset
uspto-grants-2003_06
Patent number
US06583157B2

Reaction notes

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