Toluene → 1-(3-amino-4-chlorophenyl)ethanone

HRID 1106286Notes

Reaction equation

HRID 1106286 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([N+:11]([O-])=O)[CH:5]=1)=[O:3].O.O.Cl[Sn]Cl.C1(C)C=CC=CC=1.[OH-].[Na+]>Cl.CCOCC>[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([NH2:11])[CH:5]=1)=[O:3]

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 795964'-Chloro-3'-nitroacetophenone

Product 1

HCID 27783251-(3-amino-4-chlorophenyl)ethanoneYield 87.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 39.8 g of 4-chloro-3-nitroacetophenone and 136 g of SnCl2.2H2O in 220 ml of concentrated HCl is stirred at room temperature for 0.5 hours. The reaction mixture warms spontaneously to 70° C. then cools. Toluene (200 ml) is added and the reaction mixture is made alkaline with 30% NaOH. Ether is added and the layers are separated. The aqueous layer is extracted twice more with ether, the organic layers are combined, dried, and evaporated. The solid residue is crystallized from benzene to yield 29.6 g of the title compound, melting point 104°-105° C.

Workup

  1. customwarms spontaneously to 70° C.
  2. customthe layers are separated
  3. extractionThe aqueous layer is extracted twice more with ether
  4. customdried
  5. customevaporated
  6. customThe solid residue is crystallized from benzene

Sources & evidence

ORD record
ord-dabe65c3516b4de2a373772155b49dc9
Source dataset
uspto-grants-1982_01
Patent number
US04312990

Reaction notes

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