Ethanol → HCID 118021388, compound

HRID 575621Notes

Reaction equation

HRID 575621 reaction equation
[F:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[C:14]1[C:15]([F:22])=[CH:16][C:17](=[O:21])[N:18]([CH3:20])[CH:19]=1.[Cl-].[NH4+].O.C(O)C>C1COCC1.[Fe]>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][C:3]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:2]=2[F:1])=[C:6]([C:14]2[C:15]([F:22])=[CH:16][C:17](=[O:21])[N:18]([CH3:20])[CH:19]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 118022359HCID 118022359, compound

Product 1

HCID 118021388HCID 118021388, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-[2-(2,4-difluorophenoxy)-5-nitrophenyl]-4-fluoro-1-methylpyridin-2-one (90 mg, 0.24 mmol), ammonium chloride (26 mg, 0.48 mmol), iron powder (67 mg, 1.2 mmol) suspended in THF (500 μL), water (180 mL) and ethanol (500 mL) was heated to 100° C. using microwave irradiation (normal) for 3 h. The crude reaction mixture was filtered through a short plug of celite and the celite plug was washed with heated (50° C.) MeOH (˜10 mL). The resulting filtrate was concentrated in vacuo. The resulting residue was diluted with EtOAc (20 ml) and washed with saturated bicarbonate solution (aq), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford the desired product, 5-[5-amino-2-(2,4-difluorophenoxy)phenyl]-4-fluoro-1-methylpyridin-2-one (75 mg, 90%). LCMS (M+H)+=347. The material was carried forward without any further purification.

Workup

  1. custommicrowave irradiation (normal) for 3 h
  2. customThe crude reaction mixture
  3. filtrationwas filtered through a short plug of celite
  4. washthe celite plug was washed
  5. concentrationThe resulting filtrate was concentrated in vacuo
  6. additionThe resulting residue was diluted with EtOAc (20 ml)
  7. washwashed with saturated bicarbonate solution (aq)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9cf7c664a5344702a0f02c9e0a6fa2c4
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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