Hydrazine hydrate (1:1) → HCID 63036034, compound

HRID 1853532Notes

Reaction equation

HRID 1853532 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[C:3]=1[F:18].O.NN>CO.[Ni]>[F:18][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[O:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 71015356HCID 71015356, compound

Product 1

HCID 63036034HCID 63036034, compoundYield 87.3%

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 1,2-difluoro-3-(4-nitrophenoxy)benzene (21.2 g, 84.40 mmol, 1.00 equiv) in methanol (200 mL), and Raney Nickel (2 g). A solution of hydrazine hydrate (12.67 g, 3.00 equiv) in methanol (50 mL) was added dropwise with stirring in 15 min. The resulting solution was stirred for 12 h at 25° C. The solids were filtered out and the filtrate was concentrated under vacuum. The residue was diluted with 200 mL of ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 16.3 g (87%) of 4-(2,3-difluorophenoxy)aniline as 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. filtrationThe solids were filtered out
  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-7cb3ac9372aa4896892cfaba489774ed
Source dataset
uspto-grants-2015_02
Patent number
US08962635B2

Reaction notes

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