Benzylamine → 2-benzyl-1,3(2H,4H)-isoquinolinedione

HRID 1378649Notes

Reaction equation

HRID 1378649 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]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[CH2:14]([N:21]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])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 66643Homophthalic acid

Product 1

HCID 2725142-benzyl-1,3(2H,4H)-isoquinolinedione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture consisting of homophthalic acid (25 g, 0.139 mol) and benzylamine (15.2 ml, 14.91 g, 0.139 mol) was heated at 165°-180° C. for two hours, producing a vigorous release of water vapor. Cooling afforded a hard green solid which was pulverized, triturated with diethyl ether, and isolated by filtration to afford the title compound as a light-green granular solid (29.4 g) used in the next step without further purification.

Workup

  1. temperaturewas heated at 165°-180° C. for two hours
  2. temperatureCooling
  3. customafforded a hard green solid which
  4. customtriturated with diethyl ether
  5. customisolated by filtration

Sources & evidence

ORD record
ord-7c241f42a51349d19cfe44bf24bce823
Source dataset
uspto-grants-1997_09
Patent number
US05668145

Reaction notes

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