Methyl 3-methoxy-4-methyl-2-nitrobenzoate → Methyl 2-amino-3-methoxy-4-methylbenzoate

HRID 1672479Notes

Reaction equation

HRID 1672479 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:14]([O-])=O)=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[O:7].[H][H]>C(O)C.[Pd]>[NH2:14][C:4]1[C:3]([O:2][CH3:1])=[C:12]([CH3:13])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 14543060Methyl 3-methoxy-4-methyl-2-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 14543061Methyl 2-amino-3-methoxy-4-methylbenzoateYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl 3-methoxy-4-methyl-2-nitrobenzoate (395 g, 1.75 mol) in ethanol (6700 mL) was added Pd/C (39.5 g) in one portion. The reaction mixture was stirred at room temperature under 50 psi of hydrogen overnight. TLC (petroleum ether/ethyl acetate=3:1) indicated the reaction was complete. The mixture was filtered and the filtrate was evaporated in vacuo to give the crude product, which was re-crystallized from ethanol (1.6 L) to give the title compound (321 g, 93.8%) as a white solid.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customto give the crude product, which
  4. customwas re-crystallized from ethanol (1.6 L)

Sources & evidence

ORD record
ord-98163e758ed04a5ca8339e3d9f23daae
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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