HCID 18786878, compound → HCID 18786876, compound

HRID 1107258Notes

Reaction equation

HRID 1107258 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[C:16](=[O:17])[N:15]([CH3:18])[CH:14]([N:19]([CH3:21])[CH3:20])[NH:13][C:12]2=[O:22])=[C:4]([F:23])[CH:3]=1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:23])=[C:5]([N:11]2[C:16](=[O:17])[N:15]([CH3:18])[CH:14]([N:19]([CH3:20])[CH3:21])[NH:13][C:12]2=[O:22])[CH:6]=1

Participants

5

Reactant 1

HCID 18786878HCID 18786878, compound

Product 1

HCID 18786876HCID 18786876, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a slurry of iron powder (5.3 g) in 5% aqueous acetic acid (30 mL) was added dropwise a solution of the title compound of step B (2.8 g, 8.1 mmol) in a mixture of concentrated acetic acid (25 mL) and ethyl acetate (25 mL) at room temperature. The reaction was stirred at room temperature for 30 minutes, diluted with excess ethyl acetate, filtered through Celite®, and washed with water. The aqueous phase was extracted with ethyl acetate and the combined organic layers were washed with saturated aqueous sodium bicarbonate solution and water. The organic layers were then dried over magnesium sulfate and concentrated under reduced pressure. The title compound of Step C was isolated by flash chromatography as a foam (1.59 g). 1H NMR (CDCl3) δ 7.15 (d, 1H), 6.65 (d, 1H), 3.95 (br s, 2H), 3.4 (s, 3H), 3.1 (s, 6H).

Workup

  1. filtrationfiltered through Celite®
  2. washwashed with water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic layers were washed with saturated aqueous sodium bicarbonate solution and water
  5. dry with materialThe organic layers were then dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3d1b98a2ac6044c9973d21c299376a79
Source dataset
uspto-grants-2000_05
Patent number
US06060432

Reaction notes

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