HCID 58221581, compound → HCID 58221567, compound

HRID 1475455Notes

Reaction equation

HRID 1475455 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]([C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[N+:17]([O-])=O)([CH3:9])[C:5](OC)=[O:6]>CC(O)=O.[Fe]>[CH3:1][O:2][C:3]([C:4]1([CH3:9])[C:10]2[C:11](=[CH:12][C:13]([Br:16])=[CH:14][CH:15]=2)[NH:17][C:5]1=[O:6])=[O:20]

Participants

4

Reactant 1

HCID 58221581HCID 58221581, compound

Product 1

HCID 58221567HCID 58221567, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-(4-bromo-2-nitro-phenyl)-2-methyl-malonic acid dimethyl ester (5 g, 14.4 mmol) in AcOH (30 mL) containing iron powder (2.4 g, 43.3 mmol) was stirred at 95° C. for 1 h. After that time a second aliquot of iron powder was added (803 mg, 14.4 mmol) and the stirring was maintained for an additional hour. The solvent was then removed in vacuo and the residue dissolved in EtOAc. The solid was collected by filtration and dissolved in 2 M aqueous HCl (20 mL). The mixture was stirred for 1 h at room temperature and the product was then extracted with DCM (3×). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound (2.7 g) as a white solid. MS: [M+H]+=284.

Workup

  1. temperaturethe stirring was maintained for an additional hour
  2. customThe solvent was then removed in vacuo
  3. dissolutionthe residue dissolved in EtOAc
  4. filtrationThe solid was collected by filtration
  5. dissolutiondissolved in 2 M aqueous HCl (20 mL)
  6. stirringThe mixture was stirred for 1 h at room temperature
  7. extractionthe product was then extracted with DCM (3×)
  8. dry with materialThe organic phase was dried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac1833b5bf3241f2a9fd92ed15ab934b
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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