3-Methoxyaniline → HCID 68157885, compound

HRID 243132Notes

Reaction equation

HRID 243132 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.F[C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29]>C1COCC1>[F:27][C:25]1[CH:24]=[CH:23][C:22]([N+:28]([O-:30])=[O:29])=[C:21]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:26]=1

Participants

5

Reactant 3

HCID 108243-MethoxyanilineHCID 679672,4-DifluoronitrobenzeneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 68157885HCID 68157885, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 3-methoxyphenylamine (1.58 g, 12.82 mmol) in anhydrous THF (20 mL) was cooled to −70° C. To this was added dropwise 1M LiHMDS in THF (25.14 mL, 25.14 mmol), over 10 minutes. This was stirred at −70° C. for 15 minutes before a solution of 2,4-difluoronitrobenzene (2.00 g, 12.57 mmol) in anhydrous THF (10 mL) was added dropwise. The dark yellow solution was then allowed to reach RT and was quenched with saturated aqueous NH4Cl solution. This was extracted into EtOAc (3×) and the combined organic fractions were washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a dark yellow gum, which solidified on standing (3.35 g, 100%). 1H NMR (CDCl3, 400 MHz): δ 9.60 (1H, s), 8.25 (1H, dd, J=9.48, 5.99 Hz), 7.34 (1H, t, J=8.00 Hz), 6.90-6.77 (4H, m), 6.47 (1H, ddd, J=9.47, 7.11, 2.64 Hz), 3.83 (3H, s)

Workup

  1. additionwas added dropwise
  2. customto reach RT
  3. customwas quenched with saturated aqueous NH4Cl solution
  4. extractionThis was extracted into EtOAc (3×)
  5. washthe combined organic fractions were washed with brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b35152fa5dc04e1d862741d4df6291fa
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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