HCID 12165618, compound → HCID 11513923, compound

HRID 2252020Notes

Reaction equation

HRID 2252020 reaction equation
[CH3:1][N:2]([O:17][CH3:18])[C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([N+:13]([O-])=O)[CH:5]=1>[Pd].O1CCCC1.C(O)C>[CH3:1][N:2]([O:17][CH3:18])[C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:13])[CH:5]=1

Participants

5

Reactant 1

HCID 12165618HCID 12165618, compound

Product 1

HCID 11513923HCID 11513923, compoundYield 97.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 18.0 g of 10% weight Pd/C catalyst to a solution of N-[methyl] N-[methoxy] 3,4-dinitrobenzamide (182 g, 0.712 moles) in 900 mL tetrahydrofuran and 900 mL ethanol under a nitrogen atmosphere. Hydrogenate at room temperature for 6 hours under 60 p.s.i. Filter the mixture through Celite® and concentrate the filtrate under reduced pressure. Suspend the residue in 500 mL dichloromethane, concentrate under reduced pressure and dry the residue under reduced pressure to provide 135 g (97%) of the desired compound.

Workup

  1. filtrationFilter the mixture through Celite®
  2. concentrationconcentrate the filtrate under reduced pressure
  3. concentrationconcentrate under reduced pressure
  4. customdry the residue under reduced pressure

Sources & evidence

ORD record
ord-bf6f9495d4fe491d9f5028c43ee186a3
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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