4-Chloroaniline → 1,3(2H,4H)-Isoquinolinedione, 2-(4-chlorophenyl)-

HRID 1721916Notes

Reaction equation

HRID 1721916 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=O)([OH:3])=O.[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>C1(C)C=C(C)C=C(C)C=1>[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([N:19]2[C:11](=[O:13])[CH2:10][C:5]3[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:1]2=[O:3])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 66643Homophthalic acid

Product 1

HCID 1585921,3(2H,4H)-Isoquinolinedione, 2-(4-chlorophenyl)-

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Procedure

2-(2-Carboxyphenyl)acetic acid (9 g) and 4-chloroaniline (6.3 g) in mesitylene (200 ml) were heated at reflux for 18 h, under Dean and Stark conditions. On cooling, the crude product crystallised out and was filtered off. Recrystallisation from ethanol/ethyl acetate gave 2-(4-chlorophenyl)isoquinoline-1,3(2H,4H )-dione, m.p. 178°-80° C. A mixture of this product (2.8 g) and phosphoryl chloride (10 ml) was heated at reflux for 21 h, and excess phosphoryl chloride was then eveporated at reduced pressure. The residue was stirred in ice-water for 4 h. and the precipitate filtered off and suspended in 2% aqueous sodium bicarbonate for 5 minutes. It was again filtered off, taken up in dichloromethane (150 ml) dried and evaporated. Column chromatography of the residue gave a brown solid, which was recrystallised from isooctane/ethyl acetate, to give 3-chloro-2-(4-chlorophenyl)isoquinolin-1(2H)-one m.p. 125°-7° C.

Workup

  1. temperatureat reflux for 18 h, under Dean and Stark conditions
  2. temperatureOn cooling
  3. customthe crude product crystallised out
  4. filtrationwas filtered off
  5. customRecrystallisation from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-21bb29b6d8834c788272c10029c9bbe1
Source dataset
uspto-grants-1989_08
Patent number
US04853400

Reaction notes

Loading…