Methyl 4-(1-dimethylaminomethylene-2-oxopentyl)-3-nitrobenzoate → Methyl 3-nitro-4-(2-oxopentyl)benzoate

HRID 1108703Notes

Reaction equation

HRID 1108703 reaction equation
CN(C=[C:5]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])[C:6](=[O:10])[CH2:7][CH2:8][CH3:9])C>O1CCOCC1>[N+:21]([C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:11]=1[CH2:5][C:6](=[O:10])[CH2:7][CH2:8][CH3:9])[C:15]([O:17][CH3:18])=[O:16])([O-:23])=[O:22]

Participants

3

Reactant 1

HCID 54551046Methyl 4-(1-dimethylaminomethylene-2-oxopentyl)-3-nitrobenzoate

Product 1

HCID 22627364Methyl 3-nitro-4-(2-oxopentyl)benzoateYield 89.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 4-(1-dimethylaminomethylene-2-oxopentyl)-3-nitrobenzoate (172 mg) in dioxane (9 ml) was refluxed for 4 days. The resulting mixture was evaporated in vacuo, and the residue was purified by thin layer chromatography with a mixture of hexane and ethyl acetate (2:1) to give methyl 3-nitro-4-(2-oxopentyl)benzoate (127 mg).

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue was purified by thin layer chromatography with a mixture of hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-0838b6b4349944aa9232806c3ac5cf6f
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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