1,2-Dimethoxy-4,5-dinitrobenzene → HCID 23349317, compound

HRID 614454Notes

Reaction equation

HRID 614454 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([N+:12]([O-])=O)=[CH:5][C:4]=1[O:15][CH3:16].[Br:17][CH2:18][C:19](=O)[C:20](=O)[CH3:21]>C(O)(=O)C.[Pd]>[Br:17][CH2:18][C:19]1[C:20]([CH3:21])=[N:9][C:7]2[C:6](=[CH:5][C:4]([O:15][CH3:16])=[C:3]([O:2][CH3:1])[CH:8]=2)[N:12]=1

Participants

5

Reactant 2

HCID 2229891,2-Dimethoxy-4,5-dinitrobenzeneHCID 109538801-bromobutane-2,3-dione

Product 1

HCID 23349317HCID 23349317, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

11.4 g (50 mmols) of 1,2-dimethoxy-4,5-dinitrobenzene are dissolved in 100 ml of glacial acetic acid and, after adding 0.6 g of 10% strength palladium-on-characoal, hydrogenated under normal pressure; the temperature can rise to 60° C. during the hydrogenation. Consumption of hydrogen: 7,300 ml (100% of theory). The catalyst is filtered off and the filtrate is cooled, under nitrogen, to 5° to 10° C. Whilst stirring well, 9 g (55 mmols) of 1-bromo-2,3-butanedione are added dropwise at 10° C. The solution is stirred for 60 minutes, during which time the desired product starts to precipitate out. The reaction mixture is discharged into 300 ml of cold water and the mixture is stirred for 10 minutes. The product which has precipitated is filtered off, washed with water and dried in vacuo at 60° C.

Workup

  1. customcan rise to 60° C. during the hydrogenation
  2. customConsumption of hydrogen
  3. filtrationThe catalyst is filtered off
  4. temperaturethe filtrate is cooled, under nitrogen, to 5° to 10° C

Sources & evidence

ORD record
ord-f5a3e167e8b34ca3a5fb1d561dbd8cfd
Source dataset
uspto-grants-1979_03
Patent number
US04145217

Reaction notes

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