Ethyl Acetate → HCID 21920030, compound

HRID 1823068Notes

Reaction equation

HRID 1823068 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C(OCC)(=O)C>O.C(O)(=O)C.[Fe]>[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[N:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 21920020HCID 21920020, compound

Product 1

HCID 21920030HCID 21920030, compoundYield 45.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A mixture of 0.70 g (2.8 mmol) of 2-(4-fluoro-benzyloxy)-5-nitro-pyridine and 2.36 g (4.2 mmol) of iron powder in 35 ml of water and 0.7 ml of acetic acid is heated under reflux for 4 hours. For the working-up, the reaction mixture is treated under vigorous stirring with water and ethyl acetate, thereafter, filtered over a layer of Dicalit. The organic layer is separated, dried over sodium sulfate and evaporated under reduced pressure. There are obtained 0.28 g (45% of theory) of 6-(4-fluoro-benzyloxy)-pyridin-3-ylamine as a greenish solid which is engaged in the next step without further purification.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. additionthe reaction mixture is treated
  4. filtrationfiltered over a layer of Dicalit
  5. customThe organic layer is separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8107e7856d12475eb74fc1f43f09c79f
Source dataset
uspto-grants-2006_05
Patent number
US07037935B2

Reaction notes

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