Benzoic acid, 3-methyl-2-nitro-, methyl ester → Methyl 2-nitro-3-(2-oxo-n-propyl)benzoate

HRID 274573Notes

Reaction equation

HRID 274573 reaction equation
[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C[O:16][C:17](OC)(N(C)C)[CH3:18]>CC(N(C)C)=O>[N+:12]([C:3]1[C:2]([CH2:1][C:17](=[O:16])[CH3:18])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl esterHCID 878351,1-Dimethoxyethyl(dimethyl)amine

Product 1

HCID 20093000Methyl 2-nitro-3-(2-oxo-n-propyl)benzoateYield 23%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of methyl 3-methyl-2-nitrobenzoate (1.5 g) and N,N-dimethylacetamide dimethyl acetal (3 ml) in dimethylacetamide (5 ml) was heated at 140° C. for 3 hours. After evaporation of the solvent, the resulting brown syrup was dissolved in ethyl acetate. The solution was washed with water, dried and concentrated to dryness. The residue was purified by column chromatography on silica gel to give a pale brown syrup (0.42 g, 23%).

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe resulting brown syrup was dissolved in ethyl acetate
  3. washThe solution was washed with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-fe9bd6788f2f482bad06ce005701ad2a
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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