Diisopropylaniline → 2-[2,6-Bis(1-methylethyl)phenyl]-6-chloro-1H-benz[de]isoquinoline-1,3(2H)-dione

HRID 2235985Notes

Reaction equation

HRID 2235985 reaction equation
[Cl:1][C:2]1[C:11]2[C:6]3=[C:7]([C:12]([O:14][C:15](=[O:16])[C:5]3=[CH:4][CH:3]=1)=O)[CH:8]=[CH:9][CH:10]=2.[CH:17]([C:20]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([CH3:29])[CH3:28])[C:21]=1[NH2:22])([CH3:19])[CH3:18]>CN1CCCC1=O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[Cl:1][C:2]1[C:11]2[C:6]3=[C:7]([C:12](=[O:14])[N:22]([C:21]4[C:23]([CH:27]([CH3:28])[CH3:29])=[CH:24][CH:25]=[CH:26][C:20]=4[CH:17]([CH3:19])[CH3:18])[C:15](=[O:16])[C:5]3=[CH:4][CH:3]=1)[CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 2

HCID 32484DiisopropylanilineHCID 776721H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-chloro-

Product 1

HCID 685818542-[2,6-Bis(1-methylethyl)phenyl]-6-chloro-1H-benz[de]isoquinoline-1,3(2H)-dione

Reagents, catalysts & solvents 2

HCID 11192Zinc AcetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 23.3 g of 4-chloronaphthalene-1,8-dicarboxylic anhydride, 19.0 g of 2,6-diisopropylaniline and 9.2 g of anhydrous zinc acetate in 65 ml of N-methylpyrrolidone was heated at 200° C. for 3 hours. After cooling, the precipitate formed was filtered off, washed and dried. This gave 22.4 g of 4-chloro-N-(2,6-diisopropylphenyl)naphthalene-1,8-dicarboximide having a melting point of 289° C.

Workup

  1. temperatureAfter cooling
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-752d25df81ad4b959decca6fc0907724
Source dataset
uspto-grants-2010_05
Patent number
US07714044B2

Reaction notes

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