3,5-Dichloroaniline → 4(1H)-Quinolinone, 5,7-dichloro-

HRID 1741257Notes

Reaction equation

HRID 1741257 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].CC1(C)O[C:16](=O)[CH2:15][C:13](=O)[O:12]1>>[O:12]=[C:13]1[C:3]2[C:4](=[CH:6][C:7]([Cl:9])=[CH:8][C:2]=2[Cl:1])[NH:5][CH:16]=[CH:15]1

Participants

3

Reactant 2

HCID 122813,5-DichloroanilineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 27360014(1H)-Quinolinone, 5,7-dichloro-

Procedure

Kokai Pat. No. Hei 1(1989)-246263 describes a method for producing 5,7-dichloro-4-(2-fluorophenoxy)-quinoline whereby a mixture of 3,5-dichloroaniline and Meldrum's acid is heated to give 4-oxo-5,7-dichloro-1,4-dihydroquinoline, which is reacted with phosphorus oxychloride to give 4,5,7-trichloroquinoline, which is then reacted with 2-fluorophenol to give the final compound.

Workup

  1. temperatureis heated

Sources & evidence

ORD record
ord-f6fa4de43b6a46d689c76d823b648c12
Source dataset
uspto-grants-1999_10
Patent number
US05973153

Reaction notes

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