Hydrazine hydrate (1:1) → HCID 67959904, compound

HRID 527509Notes

Reaction equation

HRID 527509 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[C:19]3[CH2:18][O:17][CH2:16][C:15]=3[CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.O.NN>C(O)C.[Pd]>[CH2:16]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([O:10][C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)[C:19]=2[CH2:18][O:17]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67960136HCID 67960136, compound2×

Product 1

HCID 67959904HCID 67959904, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-[(4-nitrophenyl)oxy]-1,3-dihydro-2-benzofuran (Intermediate 4, 208 mg), hydrazine hydrate (0.051 ml, 1.618 mmol) and Pd/C (172 mg, 0.162 mmol) in ethanol (6 ml) was stirred under argon at 90° C. After 1.5 hour the mixture was cooled to room temperature and then filtered over celite. The celite was washed with methanol. The organic phase was concentrated to afford title compound (136 mg).

Workup

  1. filtrationfiltered over celite
  2. washThe celite was washed with methanol
  3. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-4056c3aacce04316b565679e312916a6
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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