3-Chloroaniline → 2-(3-Chlorophenyl)-5,6,7,8-tetrahydro-1,3(2H,4H)-isoquinolinedione

HRID 1973888Notes

Reaction equation

HRID 1973888 reaction equation
[C:1]([OH:13])(=O)[CH2:2][CH:3]1[CH:11]=[CH:10][CH2:9][CH2:8][CH:4]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[CH2:11][CH2:10][CH2:9][CH2:8][C:4]=3[C:5]2=[O:7])[CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 79323-ChloroanilineHCID 131710580HCID 131710580, compound

Product 1

HCID 214907512-(3-Chlorophenyl)-5,6,7,8-tetrahydro-1,3(2H,4H)-isoquinolinedione

Procedure

A mixture of tetrahydrohomophthalic acid (46.0 g., 0.25 mole) and m-chloroaniline (31.8 g., 0.25 mole) is heated by an oil bath until molten for two hours. When removed from the oil bath, the reaction mixture solidifies and is recrystallized twice from ethanol/ethyl acetate, giving 2-(m-chlorophenyl)-5,6,7,8-tetrahydroisoquinoline-1,3(2H,4H)-dione.

Workup

  1. temperatureis heated by an oil bath until molten for two hours
  2. customWhen removed from the oil bath
  3. customis recrystallized twice from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-196176be78b44da582cf748758510b51
Source dataset
uspto-grants-1976_12
Patent number
US03998954

Reaction notes

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