Hydrazine hydrate (1:1) → 4-(1,3-Dihydro-2-benzofuran-5-yloxy)aniline

HRID 716824Notes

Reaction equation

HRID 716824 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:19]=[CH:18][C:14]3[CH2:15][O:16][CH2:17][C:13]=3[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.O.NN>C(O)C.[Pd]>[CH2:15]1[C:14]2[CH:18]=[CH:19][C:11]([O:10][C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)=[CH:12][C:13]=2[CH2:17][O:16]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 710901375-[(4-Nitrophenyl)oxy]-1,3-dihydro-2-benzofuran2×

Product 1

HCID 867157014-(1,3-Dihydro-2-benzofuran-5-yloxy)anilineYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A solution of 5-[(4-nitrophenyl)oxy]-1,3-dihydro-2-benzofuran (Intermediate 74, 190 mg, 0.739 mmol), hydrazine hydrate (0.046 ml, 1.477 mmol) and Pd/C (157 mg, 0.148 mmol) in ethanol (6 ml) was stirred under argon at 90° C. After 4.5 hours 0.2 equivalents of Pd/C and 2 equivalents of hydrazine hydrate were added. After 1 more hour, the reaction mixture was cooled to room temperature and then filtered over celite and washed with methanol. The organic phase was concentrated and the residue was purified by SCX to afford the title compound (152 mg).

Workup

  1. filtrationfiltered over celite
  2. washwashed with methanol
  3. concentrationThe organic phase was concentrated
  4. customthe residue was purified by SCX

Sources & evidence

ORD record
ord-69df83a1bb95442f9472e7a3ade9155f
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

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