Ammonium Chloride → 4-(Pyridin-3-Yloxy)Aniline

HRID 1515228Notes

Reaction equation

HRID 1515228 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH:2]=1.[Cl-].[NH4+]>O.O1CCCC1.CO.[Fe]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH:2]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 1199023-(4-Nitrophenoxy)pyridine

Product 1

HCID 31596314-(Pyridin-3-Yloxy)AnilineYield 36%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

4-(Pyridin-3-yl)oxy-1-nitrobenzene prepared in Step A was dissolved in the mixture of water (100 mL), tetrahydrofuran (100 mL) and methanol (100 mL). Iron powder (103 g, 1.84 mol) and ammonium chloride (99 g, 1.84 mol) were added thereto, and the mixture was stirred for 3 h at 80° C. using a mechanical stirrer. After completion of the reaction, the reaction mixture was filtered through a cellite, washed with methanol, and concentrated under reduced pressure. The solid thus obtained was filtered, washed with ether, and dried to give the title compound (17 g, Yield 36%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through a cellite
  3. washwashed with methanol
  4. concentrationconcentrated under reduced pressure
  5. customThe solid thus obtained
  6. filtrationwas filtered
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-67ee1148b03b406f96dcbf466b0cc7c1
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

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