N-[4-(3-fluoro-4-nitro-anilino)-2-pyridyl]cyclopropanecarboxamide → N-[4-(4-amino-3-fluoro-anilino)-2-pyridyl]cyclopropanecarboxamide

HRID 2200114Notes

Reaction equation

HRID 2200114 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[N+:21]([O-])=O)[NH:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:13]([CH:15]2[CH2:17][CH2:16]2)=[O:14])[CH:7]=1>CO.[Pd]>[NH2:21][C:20]1[CH:19]=[CH:18][C:4]([NH:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])[CH:7]=2)=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 90020584N-[4-(3-fluoro-4-nitro-anilino)-2-pyridyl]cyclopropanecarboxamide

Product 1

HCID 90020682N-[4-(4-amino-3-fluoro-anilino)-2-pyridyl]cyclopropanecarboxamideYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve N-[4-(3-fluoro-4-nitro-anilino)-2-pyridyl]cyclopropanecarboxamide (160 mg, 0.51 mmol) in methanol (10 mL), add wet Pd/C (10%, 60 mg), flush with H2 and then stir the reaction under H2 atmosphere at room temperature for 6 hrs. Remove H2, filter the mixture. Concentrate the filtrate under reduced pressure to give the crude product (140 mg) which is used directly without further purification. MS: (M+1): 287.2.

Workup

  1. customflush with H2
  2. customthe reaction under H2 atmosphere at room temperature for 6 hrs
  3. filtrationRemove H2, filter the mixture
  4. concentrationConcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-b0bbb366359e4f948f8efcd16a540b03
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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