Water → 7-(4-amino-2-fluorophenoxy)-N',N'-dimethylthieno[3,2-b]pyridine-2-carbohydrazide

HRID 418674Notes

Reaction equation

HRID 418674 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]([NH:16][N:17]([CH3:19])[CH3:18])=[O:15])[S:13][C:6]=12.[NH4+].[Cl-].O>CCO.[Fe]>[NH2:24][C:22]1[CH:21]=[CH:20][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]([NH:16][N:17]([CH3:19])[CH3:18])=[O:15])[S:13][C:6]=23)=[C:2]([F:1])[CH:23]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 587900077-(2-fluoro-4-nitrophenoxy)-N',N'-dimethylthieno[3,2-b]pyridine-2-carbohydrazide

Product 1

HCID 587902227-(4-amino-2-fluorophenoxy)-N',N'-dimethylthieno[3,2-b]pyridine-2-carbohydrazideYield 85.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 7-(2-fluoro-4-nitrophenoxy)-N′,N′-dimethylthieno[3,2-b]pyridine-2-carbohydrazide 238 (772 mg, 2.05 mmol) and NH4Cl (93 mg, 1.74 mmol) in EtOH (20.5 mL)/water (10.3 mL) at 100° C., Fe (973 mg, 17.73 mmol) was added in one portion and the mixture was heated to reflux with vigorous stirring 40 min. The mixture was filtered through Celite®, the Celite® washed with EtOH and the combined organic solutions concentrated under reduced pressure. The residue was purified by flash chromatography (MeOH/DCM 1:9) giving 239 (605 mg, 1.75 mmol, 85%). MS (m/z): (M+1) 347.0 (100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. filtrationThe mixture was filtered through Celite®
  4. washthe Celite® washed with EtOH
  5. concentrationthe combined organic solutions concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (MeOH/DCM 1:9)

Sources & evidence

ORD record
ord-4315f5f8bc994b7db1946777988378f0
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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