Methyl 2,4-dimethyl-3-nitrobenzoate → Methyl 3-amino-2,4-dimethylbenzoate

HRID 239920Notes

Reaction equation

HRID 239920 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([CH3:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CO.[Pd]>[NH2:12][C:11]1[C:2]([CH3:1])=[C:3]([CH:8]=[CH:9][C:10]=1[CH3:15])[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 71744216Methyl 2,4-dimethyl-3-nitrobenzoate

Product 1

HCID 66871802Methyl 3-amino-2,4-dimethylbenzoateYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2,4-dimethyl-3-nitro-benzoate (37 g, 176.9 mmol) in methanol (370 mL), 10% palladium on carbon 50% wet (5.6 g) is added. The reaction is bubbled with hydrogen and placed under a hydrogen atmosphere for 6 days. The mixture is filtered through diatomaceous earth and the filtrate is evaporated to dryness. The resulting residue is purified by flash chromatography (silica gel), eluting with 20% ethyl acetate in hexanes to afford the title compound as a yellow oil (20.5 g, 65%). Mass spectrum (m/z): 180.1 (M+1). 1H NMR (300.16 MHz, DMSO-d6): δ 6.89 (s, 2H), 4.78 (s, 2H), 3.76 (s, 3H), 2.23 (s, 3H), 2.12 (s, 3H).

Workup

  1. customThe reaction is bubbled with hydrogen
  2. filtrationThe mixture is filtered through diatomaceous earth
  3. customthe filtrate is evaporated to dryness
  4. customThe resulting residue is purified by flash chromatography (silica gel)
  5. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e9fb16a0c12644bb996ecd7378867b37
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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