Hydrazine hydrate (1:1) → 4-(2,3-dimethylphenoxy)aniline

HRID 1023558Notes

Reaction equation

HRID 1023558 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=2[CH3:18])=[CH:6][CH:5]=1)([O-])=O.O.NN>C(O)C.[Pd]>[CH3:18][C:12]1[C:13]([CH3:17])=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 6181291,2-Dimethyl-3-(4-nitrophenoxy)benzene2×

Product 1

HCID 71392004-(2,3-dimethylphenoxy)anilineYield 105%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

2,3-dimethylphenyl 4-nitrophenyl ether (Intermediate 73, 865 mg) was dissolved in ethanol (10 mL) to give a pale yellow solution. Hydrazine hydrate 50% (0.698 mL, 7.1 mmol) and Pd/C (37.8 mg, 0.36 mmol) were added. The reaction mixture was stirred at 90° C. for 1 hour. The reaction mixture was filtered and the organic phase was evaporated under vacuum to afford the title compound as a pale yellow oil (796 mg).

Workup

  1. customto give a pale yellow solution
  2. filtrationThe reaction mixture was filtered
  3. customthe organic phase was evaporated under vacuum

Sources & evidence

ORD record
ord-db795b4f4c3c4a0cb3e273ed002f88ad
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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