Methyl 4-methyl-3,5-dinitrobenzoate → Methyl 3-amino-4-methyl-5-nitrobenzoate

HRID 852594Notes

Reaction equation

HRID 852594 reaction equation
[CH3:1][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.C1CCCCC=1.[Pd]>[NH2:15][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:2]=1[CH3:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 1

HCID 4366501Methyl 4-methyl-3,5-dinitrobenzoate

Product 1

HCID 839285Methyl 3-amino-4-methyl-5-nitrobenzoateYield 83,735.102%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8079CyclohexeneSolvent

Procedure

To a solution of methyl 4-methyl-3,5-dinitrobenzoate (D162) (30 g, 0.125 mmol, 1 equiv) in MeOH (150 ml) and cyclohexene (300 ml) was added 10% palladium on charcoal (50% wet, 3 g, 5% w/w) and the resulting suspension was refluxed for 7 h then cooled to room temperature. The catalyst was filtered off through a pad of celite and most of the solvent was removed in vacuo. The precipitate formed was filtered off to give methyl 3-amino-4-methyl-5-nitrobenzoate (D196) (22 g, 84%) as a yellow solid which was used in the next step without further purification. [M+H]+=211.0, RT=2.81 min.

Workup

  1. temperaturethe resulting suspension was refluxed for 7 h
  2. filtrationThe catalyst was filtered off through a pad of celite and most of the solvent
  3. customwas removed in vacuo
  4. customThe precipitate formed
  5. filtrationwas filtered off

Sources & evidence

ORD record
ord-8cff88bac1754dcc8a73159e4294f619
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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