Pyridine → 3'-Chloro-4'-aminoacetophenone

HRID 1607657Notes

Reaction equation

HRID 1607657 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl-:17].[Cl-].IC1C=CC=CC=1>O1CCCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[Cl:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7468p-AminoacetophenoneHCID 13166207CID 13166207

Product 1

HCID 2368013'-Chloro-4'-aminoacetophenoneYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of p-aminoacetophenone (20 g), pyridine (11.7 g), and iodobenzene dichloride (40 g) in tetrahydrofuran (300 ml) was stirred for 5 hours at 0° C. The insoluble materials were filtered, and the filtrate was concentrated under reduced pressure. The residue obtained was crystallized from ethanol to give colorless crystals of 4'-amino-3'-chloroacetophenone (20.1 g).

Workup

  1. filtrationThe insoluble materials were filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue obtained
  4. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-361c68959f6f42ddaf5135e16251f5bc
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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