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

HRID 1835516Notes

Reaction equation

HRID 1835516 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 (186.1) (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 hr. After cooling the reaction mixture was filtered through short celite pad. The filtrate was concentrated, diluted with sat. NaHCO3 and extacted 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 (silicagel, AcOEt:Hexane=1:3) to provide aniline 186.2 (0.420 g) as a colorless solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hr
  3. temperatureAfter cooling the reaction mixture
  4. filtrationwas filtered through short celite pad
  5. concentrationThe filtrate was concentrated
  6. additiondiluted with sat. NaHCO3
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. customConcentration of solvent afford crude product, which
  10. customwas purified by column chromatography (silicagel, AcOEt:Hexane=1:3)

Sources & evidence

ORD record
ord-e69f9be9b1e14180a77a07f67d1e2ce0
Source dataset
uspto-grants-2004_08
Patent number
US06770648B2

Reaction notes

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