Pyridine → Methyl 4-(2-oxobutyl)-3-nitrobenzoate

HRID 1242124

Reaction equation

HRID 1242124 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16].N1[CH:24]=[CH:23]C=CC=1.C(Cl)(=[O:28])CC.C(Cl)Cl>O.O1CCOCC1>[O:28]=[C:3]([CH2:23][CH3:24])[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 62324Propionyl chlorideHCID 894337(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

Product 1

HCID 21938235Methyl 4-(2-oxobutyl)-3-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

According to the method of Production Example 1, a mixed solution of methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (6.30 g), pyridine (3.2 ml), propionyl chloride (3.26 g) and methylene chloride (60 ml) is heated under reflux for 11 hours, and then heated under reflux with 1,4-dioxane in water for 16 hours to obtain methyl 4-(2-oxobutyl)-3-nitrobenzoate (5.63 g).

Workup

  1. temperatureunder reflux for 11 hours
  2. temperatureheated

Sources & evidence

ORD record
ord-44241f6f06f8418bbcc629a864c0f360
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Linked notes

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