Water → HCID 67434358, compound

HRID 2036619Notes

Reaction equation

HRID 2036619 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.O>CC(O)=O.[Fe]>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:12]=[CH:13][CH:14]=[C:15]([NH2:16])[CH:10]2[NH2:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 67431500HCID 67431500, compound

Product 1

HCID 67434358HCID 67434358, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(3,5-difluorophenyl)-3-nitro-pyridin-2-amine (2.0 g, 7.96 mmol) in AcOH (24 mL) was added iron powder (1.33 g, 23.8 mmol) and the reaction mixture was heated to 100° C. for 1 h. The reaction mixture was cooled to rt and water (70 mL) was added. The organic layer was extracted with EtOAc (350 mL) and was basified by using satd. sodium bicarbonate solution (150 mL), dried over sodium sulfate and concentrated in vacuo to provide N1-(3,5-Difluorophenyl)-pyridine-2,3-diamine. The crude product was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionThe organic layer was extracted with EtOAc (350 mL)
  3. dry with materialsodium bicarbonate solution (150 mL), dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1dd91790eb6d4ef286525ee79fcdc3fa
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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