1,3,5-trimethoxy-2,4-dinitrobenzene → HCID 23009735, compound

HRID 359638Notes

Reaction equation

HRID 359638 reaction equation
[N+:1]([C:4]1[C:9]([O:10][CH3:11])=[C:8]([N+:12]([O-])=O)[C:7]([O:15][CH3:16])=[CH:6][C:5]=1[O:17][CH3:18])([O-:3])=[O:2].[PH2]([O-])=O.[Na+]>[Pd].O1CCCC1.O>[NH2:12][C:8]1[C:9]([O:10][CH3:11])=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([O:17][CH3:18])=[CH:6][C:7]=1[O:15][CH3:16]

Participants

6

Reactant 2

HCID 27749591,3,5-trimethoxy-2,4-dinitrobenzeneHCID 178527019HCID 178527019, compound

Product 1

HCID 23009735HCID 23009735, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 26 g of palladium on charcoal (10%) is refluxed in 1.3 l of tetrahydrofuran and 26 ml of water containing 1 mole (258 g) of 2,4-dinitro-1,3,5-trimethoxybenzene. A solution of 247 g of sodium hypophosphite in 260 ml of water is added to this suspension over 3 hours. Refluxing is continued for an additional 30 minutes. After cooling, the catalyst is removed by filtration and the aqueous phase by phase separation. The organic phase is concentrated under vacuum and is then poured onto ice. The expected product precipitates. It melts at 111° C.

Workup

  1. temperatureRefluxing
  2. temperatureAfter cooling
  3. customthe catalyst is removed by filtration
  4. customthe aqueous phase by phase separation
  5. concentrationThe organic phase is concentrated under vacuum
  6. additionis then poured onto ice
  7. customThe expected product precipitates

Sources & evidence

ORD record
ord-53212ae6178b46fab4b2a15b4a3f3c7b
Source dataset
uspto-grants-1991_03
Patent number
US05002585

Reaction notes

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