Dimethyl 3-oxoglutarate → HCID 178500929, compound

HRID 386545Notes

Reaction equation

HRID 386545 reaction equation
[O:1]=[C:2]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C([O-])(=O)C.[Na+].[Cl:18][C:19]1[CH:20]=[C:21]([N+:26]#[N:27])[CH:22]=[CH:23][C:24]=1[Cl:25]>C(O)C.O>[Cl:18][C:19]1[CH:20]=[C:21]([NH:26]/[N:27]=[C:8](\[C:2](=[O:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5])/[C:9]([O:11][CH3:12])=[O:10])[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

6

Reactant 3

HCID 74591Dimethyl 3-oxoglutarateHCID 517045Sodium AcetateHCID 102625163,4-Dichlorobenzenediazonium

Product 1

HCID 178500929HCID 178500929, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of dimethyl 3-oxopentanedioate (3.48 g, 20 mmol) in ethanol (12 mL) and water (40 mL) at room temperature was added sodium acetate (12.0 g, 146 mmol), and was followed by the addition of 3,4-dichlorobenzenediazonium solution (20 mmol). The resulting reaction mixture was stirred at room temperature for 1 h. The product was collected by filtration, then washed with water (˜50 mL) and dried overnight under reduced pressure to yield 6.776 g (93%) of (E)-dimethyl 2-(2-(3,4-dichlorophenyl)hydrazono)-3-oxopentanedioate as a yellow solid. MS (ESI) 347 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe product was collected by filtration
  3. washwashed with water (˜50 mL)
  4. customdried overnight under reduced pressure

Sources & evidence

ORD record
ord-c873085dc87b4b42b97ef6b2fca382fc
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

Loading…