HCID 67232190, compound → HCID 15056849, compound

HRID 733105Notes

Reaction equation

HRID 733105 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9](OC)=[O:10])=[C:4]([N+:15]([O-])=O)[CH:3]=1>C(O)(=O)C.[Fe]>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8]([CH3:14])([CH3:13])[C:9](=[O:10])[NH:15]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 67232190HCID 67232190, compound

Product 1

HCID 15056849HCID 15056849, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 2-(4-fluoro-2-nitrophenyl)-2-methylpropanoate (2.53 g, 0.010 mol, step 1 of Example 15) and iron powder (2.34 g, 0.042 mol) in acetic acid (30 mL) was stirred at 100° C. for 5.5 h. The reaction mixture was rinsed with methanol and it was filtered through a pad of Celite. The filtrate was concentrated. It was added water and the aqueous layer was extracted with ethyl acetate (20 mL×3). The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:6 to 1:4) to give 1.67 g (89%) of the title compound as a white solid.

Workup

  1. washThe reaction mixture was rinsed with methanol and it
  2. filtrationwas filtered through a pad of Celite
  3. concentrationThe filtrate was concentrated
  4. additionIt was added water
  5. extractionthe aqueous layer was extracted with ethyl acetate (20 mL×3)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:6 to 1:4)

Sources & evidence

ORD record
ord-1485252af8ef49979df9dfdb25a6cdef
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

Loading…