Chloranil → 4-Bromo-6,6-dimethyl-2-(4-methyl-3-nitrophenyl)-3,6-dihydro-7H-imidazo[4,5-h]isoquinoline-7,9(8H)-dione

HRID 2253306Notes

Reaction equation

HRID 2253306 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]2[C:5]([C:6]([CH3:16])([CH3:15])[C:7](=[O:14])[NH:8][C:9]2=[O:13])=[CH:4][C:3]=1[Br:17].[CH3:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][C:20]=1[N+:27]([O-:29])=[O:28].C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>CC#N.CN(C=O)C>[Br:17][C:3]1[C:2]2[N:1]=[C:23]([C:22]3[CH:25]=[CH:26][C:19]([CH3:18])=[C:20]([N+:27]([O-:29])=[O:28])[CH:21]=3)[NH:12][C:11]=2[C:10]2[C:9](=[O:13])[NH:8][C:7](=[O:14])[C:6]([CH3:15])([CH3:16])[C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 8371ChloranilHCID 17989983-Nitro-p-tolualdehydeHCID 596454907,8-Diamino-6-bromo-4,4-dimethylisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 454867184-Bromo-6,6-dimethyl-2-(4-methyl-3-nitrophenyl)-3,6-dihydro-7H-imidazo[4,5-h]isoquinoline-7,9(8H)-dioneYield 79.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 7,8-diamino-6-bromo-4,4-dimethylisoquinoline-1,3(2H,4H)-dione (1.40 g, 4.70 mmol) in MeCN (47 mL) and DMF (3 mL) was added 4-methyl-3-nitro-benzaldehyde (814.2 mg, 4.93 mmol) and p-chloranil (1.21 g, 4.93 mmol). The reaction mixture was stirred at 60° C. for 8 h. The cooled mixture was diluted with MeCN (50 mL) and the suspension was filtered. The solid was dried to give the title compound (1.65 g, 79% yield).

Workup

  1. filtrationthe suspension was filtered
  2. customThe solid was dried

Sources & evidence

ORD record
ord-c3e4aca176994d9fb53b265da772ebf7
Source dataset
uspto-grants-2008_01
Patent number
US07323567B2

Reaction notes

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