Water → (3-Aminophenyl)-3-pyridinylmethanone

HRID 1603770Notes

Reaction equation

HRID 1603770 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[C:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:8])([O-])=O.[Sn](Cl)Cl.O.[OH-].[Na+]>C(O)C.Cl>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[C:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 12930027HCID 12930027, compound

Product 1

HCID 12930028(3-Aminophenyl)-3-pyridinylmethanoneYield 95.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

3-(3-Nitrobenzoyl)pyridine (1.55 g, 0.006 mole) was suspended in ethanol (35 ml) and treated portionwise with a solution of tin (11) chloride (4.56, 0.024 mmole) in conc. HCl (7 ml). The reaction mixture was stirred at 50° C. for 2 hours. After allowing to cool to room temperature, water (50 ml) was added and the mixture basified with 10% aqueous sodium hydroxide, extracted into ethyl acetate, dried (Na2SO4) and evaporated in vacuo to afford the title compound (1.14 g, 85%) as a pale oil

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted into ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-fef7611c4d46457c86bb3a4a3a774e50
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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