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

HRID 1973881Notes

Reaction equation

HRID 1973881 reaction equation
[C:1]([OH:13])(=O)[CH2:2][C:3]1[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:5]([OH:7])=O.[Cl:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18]>>[Cl:14][C:15]1[CH:16]=[C:17]([N:18]2[C:1](=[O:13])[CH2:2][C:3]3[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:5]2=[O:7])[CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 79323-ChloroanilineHCID 66643Homophthalic acid

Product 1

HCID 1854844H-Isoquinoline-1,3-dione, 2-(3-chlorophenyl)-Yield 58%

Procedure

A mixture of homophthalic acid (45.0 g., 0.25 mole) and m-chloroaniline (31.8 g., 0.25 mole) was heated by an oil bath to 175°-180° C. for two hours. When removed from the oil bath, the reaction mixture solidified and was recrystallized twice from ethanol/ethyl acetate, giving 2-(m-chlorophenyl)-isoquinoline-1,3 (2H, 4H)-dione, 36.0 g. (58% yield), m.p. 160°-161° C.

Workup

  1. temperaturewas heated by an oil bath to 175°-180° C. for two hours
  2. customWhen removed from the oil bath
  3. customthe reaction mixture solidified and was recrystallized twice from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-ac7b1461ffd144828ba9ee4264173fca
Source dataset
uspto-grants-1976_12
Patent number
US03998954

Reaction notes

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