HCID 69417845, compound → HCID 69418409, compound

HRID 1293295Notes

Reaction equation

HRID 1293295 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:3]=1[O:4][C:5]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]>CO.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:5]([O:4][C:3]2[C:18]([F:22])=[CH:19][CH:20]=[CH:21][C:2]=2[F:1])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 69417845HCID 69417845, compound

Product 1

HCID 69418409HCID 69418409, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of methyl 2-(2,6-difluorophenoxy)-5-nitrobenzoate (step 1, 365 mg, 1.18 mmol) and 5% Pd/C (37 mg) in methanol (10 mL) was stirred under hydrogen atmosphere for 16 h at room temperature. After filtration through a pad of Celite®, the filtrate was concentrated. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (5/1 to 1/2) to afford 325 mg of the title compound: 1H-NMR (CDCl3) δ 7.21 (1H, d, J=2.9 Hz), 7.12–6.88 (3H, m), 6.77 (1H, dd, J=8.8, 2.9 Hz), 6.64–6.58 (1H, m), 3.87 (3H, s).

Workup

  1. filtrationAfter filtration through a pad of Celite®
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (5/1 to 1/2)

Sources & evidence

ORD record
ord-de7746d3d16a4d77be09cc1006dc6dbb
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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