Hydrazine → 2-Nitro-4-(oxetan-3-YL)aniline

HRID 511666Notes

Reaction equation

HRID 511666 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([CH:10]2[CH2:13][O:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[NH:14]C(=O)C)([O-:3])=[O:2].NN>>[N+:1]([C:4]1[CH:9]=[C:8]([CH:10]2[CH2:11][O:12][CH2:13]2)[CH:7]=[CH:6][C:5]=1[NH2:14])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 9321HydrazineHCID 67776164N-(2-nitro-4-(oxetan-3-yl)phenyl)acetamide

Product 1

HCID 677751732-Nitro-4-(oxetan-3-YL)anilineYield 69.1%

Conditions

Temperature
70 °C

Procedure

A suspension of N-(2-nitro-4-oxetan-3-ylphenyl)acetamide (125 mg, 0.529 mmo) in aqueous hydrazine (8 ml, 160 mmol) was heated at 70° C. for 2 h, the reaction mixture was cooled to 45° C. and the hydrazine was removed in vacuo to yield a solid. The crude material was purified by flash chromatography (SiO2, eluting with 20% EtOAc/CH2Cl2 to yield the desired product (71 mg).

Workup

  1. temperaturethe reaction mixture was cooled to 45° C.
  2. customthe hydrazine was removed in vacuo
  3. customto yield a solid
  4. customThe crude material was purified by flash chromatography (SiO2
  5. washeluting with 20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-5f0508cb6a344463b80dce75f9d7ab4e
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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