Hydrazine hydrate (1:1) → HCID 83396832, compound

HRID 2207484Notes

Reaction equation

HRID 2207484 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1.O.NN>CO.[Ni]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[O:9][C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 138436881,3-Difluoro-2-(4-nitrophenoxy)benzene

Product 1

HCID 83396832HCID 83396832, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

Into a 500 mL, 3-necked round-bottom flask purged and maintained under an inert atmosphere of nitrogen, was placed a solution of 1,3-difluoro-2-(4-nitrophenoxy)benzene (20 g, 79.62 mmol, 1.00 equiv) in methanol (200 mL), Raney Nickel (2 g). A solution of hydrazine hydrate (12.67 g) in methanol (50 mL) was added dropwise with stirring in 15 min. The resulting solution was stirred for 12 h at 25° C., then filtrated and the filtrate was concentrated under vacuum. The residue was diluted with 200 mL of ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate and concentrated under vacuum to give 16 g (91%) of 4-(2,6-difluorophenoxy)aniline as a black oil.

Workup

  1. customInto a 500 mL, 3-necked round-bottom flask purged
  2. temperaturemaintained under an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred for 12 h at 25° C.
  4. filtrationfiltrated
  5. concentrationthe filtrate was concentrated under vacuum
  6. additionThe residue was diluted with 200 mL of ethyl acetate
  7. washwashed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dc4918d37fa545c9adc6776a58dcc967
Source dataset
uspto-grants-2016_06
Patent number
US09376438B2

Reaction notes

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