HCID 4912811, compound → HCID 69356421, compound

HRID 852600Notes

Reaction equation

HRID 852600 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:15]([O-])=O>CO.C1CCCCC1.[Pd]>[NH2:15][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:2]=1[NH2:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 1

HCID 4912811HCID 4912811, compound

Product 1

HCID 69356421HCID 69356421, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8078CyclohexaneSolvent

Procedure

To a solution of methyl 4-amino-3,5-dinitrobenzoate (D203) (3.0 g, 12.4 mmol, 1 equiv) in MeOH (40 ml) and cyclohexane (80 ml) was added 10% palladium on charcoal (50% wet, 2.0 g, 33% w/w) and the resulting mixture was refluxed for 30 min then cooled to room temperature. The catalyst was filtered off through a pad of celite and washed with DMF. The combined organic phases were concentrated in vacuo and the residue triturated with Et2O/iso-hexane to give methyl 3,4-diamino-5-nitrobenzoate (D204) (2.1 g, 80%) as a red solid which was used in the next step without further purification. [M+H]+=212.2, RT=2.46 min.

Workup

  1. temperaturethe resulting mixture was refluxed for 30 min
  2. filtrationThe catalyst was filtered off through a pad of celite
  3. washwashed with DMF
  4. concentrationThe combined organic phases were concentrated in vacuo
  5. customthe residue triturated with Et2O/iso-hexane

Sources & evidence

ORD record
ord-3c8f7db4479a4d6182cdcaa900a52314
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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