Hydrazine hydrate (1:1) → 4-Methoxydibenzofuran-1-amine

HRID 1293441Notes

Reaction equation

HRID 1293441 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1.O.[NH2:17]N>CO.[Ni]>[NH2:17][C:6]1[C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 119941974-Methoxydibenzofuran

Product 1

HCID 4593564-Methoxydibenzofuran-1-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Intermediate 38 (550 mg, 2.26 mmol) was taken in methanol (10 ml) and raney nickel catalyst (100 mg, 18% w/w) was added. The reaction mixture was refluxed and to this was added hydrazine hydrate (99%) solution (2 ml) slowly over a period of 10 min. The refluxing continued for 2 h. The catalyst was filtered and the filterate was concentrated and diluted with water (100 ml) and further extracted with ethyl acetate (3×25 ml). The organic layer was washed with water and concentrated to give the product as brown solid (500 mg);mp: 167-169° C.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. filtrationThe catalyst was filtered
  3. concentrationthe filterate was concentrated
  4. additiondiluted with water (100 ml)
  5. extractionfurther extracted with ethyl acetate (3×25 ml)
  6. washThe organic layer was washed with water
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ccaeb670cfdf4335abc3bac193efc50d
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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