Benzoyl chloride → 4,4-dimethyl-7-benzoylamino-8-nitro-2H,4H-isoquinoline-1,3-dione

HRID 47104Notes

Reaction equation

HRID 47104 reaction equation
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[C:7]([N+:16]([O-:18])=[O:17])[C:8]([NH:12][C:13]([CH3:15])=[O:14])=[CH:9][CH:10]=2)[C:5](=[O:19])[NH:4][C:3]1=[O:20].C(Cl)(=O)[C:23]1[CH:28]=[CH:27]C=[CH:25][CH:24]=1>C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[C:7]([N+:16]([O-:18])=[O:17])[C:8]([NH:12][C:13](=[O:14])[C:15]3[CH:27]=[CH:28][CH:23]=[CH:24][CH:25]=3)=[CH:9][CH:10]=2)[C:5](=[O:19])[NH:4][C:3]1=[O:20]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 118331714,4-dimethyl-7-acetamino-8-nitro-2H,4H-isoquinoline-1,3-dione

Product 1

HCID 203850054,4-dimethyl-7-benzoylamino-8-nitro-2H,4H-isoquinoline-1,3-dioneYield 68%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

43.8 gm of 4,4-dimethyl-7-acetamino-8-nitro-2H,4H-isoquinoline-1,3-dione were admixed with 200 gm of xylene with 104 gm of benzoyl chloride, and the mixture was refluxed for 10 hours while stirring. After cooling, the reaction mixture was suction-filtered, and the filter cake was washed with toluene and petroleum ether, yielding 36 gm (68% of theory) of 4,4-dimethyl-7-benzoylamino-8-nitro-2H,4H-isoquinoline-1,3-dione, m.p. above 270° C.

Workup

  1. temperaturethe mixture was refluxed for 10 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was suction-filtered
  4. washthe filter cake was washed with toluene and petroleum ether

Sources & evidence

ORD record
ord-1d4d96e0c7894d34b2e90d47e9a1adb7
Source dataset
uspto-grants-1979_11
Patent number
US04176184

Reaction notes

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