Ethyl 3-methyl-2-nitrobenzoate → HCID 20093050, compound

HRID 274575Notes

Reaction equation

HRID 274575 reaction equation
[CH3:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C([O:18][C:19](OCC)(N(C)C)[CH2:20][CH3:21])C>C(OCC)(=O)C>[N+:13]([C:3]1[C:2]([CH2:1][C:19](=[O:18])[CH2:20][CH3:21])=[CH:12][CH:11]=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6])([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 20093011Ethyl 3-methyl-2-nitrobenzoateHCID 20093027HCID 20093027, compound

Product 1

HCID 20093050HCID 20093050, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
145 °C

Procedure

A stirred mixture of ethyl 3-methyl-2-nitrobenzoate (0.96 g) and N,N-dimethylpropionamide diethyl acetal (2.3 g) was heated at 145° C. for 36 hours. The reaction mixture was dissolved in ethyl acetate. The solution was washed with dilute hydrochloric acid and then water, dried and concentrated to dryness. The residue was purified by column chromatography on silica gel to give a pale brown syrup (0.36 g, 33%).

Workup

  1. washThe solution was washed with dilute hydrochloric acid
  2. dry with materialwater, dried
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-21fff84c6078487a99af7568e10a21df
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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