HCID 67063017, compound → HCID 67063163, compound

HRID 599268Notes

Reaction equation

HRID 599268 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:4]([CH3:18])[CH:3]=1>CC(O)=O.[Fe]>[NH2:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([CH3:18])=[C:5]([C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=1

Participants

4

Reactant 1

HCID 67063017HCID 67063017, compound

Product 1

HCID 67063163HCID 67063163, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 2-(4-fluoro-2-methyl-5-nitrophenyl)-2-oxoacetate (15 g, 59 mmol) and Fe (46 g, 828 mmol) in AcOH (200 mL) was stirred at RT overnight. The solid was removed by filtration, and the solvent was removed under reduced pressure. The residue was partitioned with water and EtOAc. The organic layer was washed with brine, dried (MgSO4), and concentrated in vacuo to give ethyl 2-(5-amino-4-fluoro-2-methylphenyl)-2-oxoacetate (9.0 g, 70% yield), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 7.16 (d, J=6.9 Hz, 1 H), 6.91 (d, J=8.7 Hz, 1 H), 4.41 (q, J=7.2 Hz, 2 H), 2.50 (s, 3 H), 1.40 (t, J=7.2 Hz, 3 H).

Workup

  1. customThe solid was removed by filtration
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was partitioned with water and EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a522802cb9b94a01bf22ffb2a6bd3011
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

Loading…