Allylamine → 2-(2-Propen-1-yl)-1,3(2H,4H)-isoquinolinedione

HRID 1973882Notes

Reaction equation

HRID 1973882 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.[CH2:14]([NH2:17])[CH:15]=[CH2:16]>>[CH2:14]([N:17]1[C:1](=[O:13])[CH2:2][C:3]2[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5]1=[O:7])[CH:15]=[CH2:16]

Participants

3

Reactant 2

HCID 7853AllylamineHCID 66643Homophthalic acid

Product 1

HCID 581581112-(2-Propen-1-yl)-1,3(2H,4H)-isoquinolinedioneYield 46%

Procedure

A mixture of homophthalic acid (9.0 g., 0.05 mole) and allylamine (2.8 g., 0.05 mole) was heated by an oil bath to 185°-190° C. for 40 minutes. The mixture solidified upon cooling, and was recrystallized twice from isopropanol, giving 2-allylisoquinoline-1,3 (2H, 4H)-dione, 4.6 g. (46% yield), m.p. 75°-77° C.

Workup

  1. temperaturewas heated by an oil bath to 185°-190° C. for 40 minutes
  2. temperatureupon cooling
  3. customwas recrystallized twice from isopropanol

Sources & evidence

ORD record
ord-499637d930e64a4793b5f8d95a329532
Source dataset
uspto-grants-1976_12
Patent number
US03998954

Reaction notes

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