Hydrazine → 4-(tert-Butyl)-3-methoxyaniline

HRID 1465124Notes

Reaction equation

HRID 1465124 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:7][C:6]=1[O:22][CH3:23])([CH3:4])([CH3:3])[CH3:2].NN>C(O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[O:22][CH3:23])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 593949542-(4-Tert-butyl-3-methoxyphenyl)isoindoline-1,3-dione

Product 1

HCID 574701524-(tert-Butyl)-3-methoxyanilineYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A slurry of 2-(4-tert-butyl-3-methoxy-phenyl)isoindoline-1,3-dione (400 mg, 1.29 mmol) and NH2NH2 (207 mg, 203 μL, 6.47 mmol) in ethanol (10 mL) was refluxed for 3 h. The reaction was cooled and concentrated in vacuo. The residue was extracted with water (25 mL) and ethyl acetate (3×10 mL). The combined organic extracts were washed with water, dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (25-40% ethyl acetate/hexanes) provided 4-tert-butyl-3-methoxy-aniline (190 mg, 82% yield) as light brown oil. 1H NMR (400.0 MHz, CDCl3) δ 6.97 (d, J=8.1 Hz, 1H), 6.17 (m, 2H), 3.71 (d, J=3.3 Hz, 3H), 3.53 (br s, 2H), 1.25 (d, J=3.3 Hz, 9H).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. extractionThe residue was extracted with water (25 mL) and ethyl acetate (3×10 mL)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (25-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ca148ebbfd724e37ad75d644a427f552
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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