2,3-Dihydro-7-nitrobenzofuran → 2,3-Dihydro-1-benzofuran-7-amine

HRID 1155567Notes

Reaction equation

HRID 1155567 reaction equation
[N+:1]([C:4]1[C:12]2[O:11][CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[H][H]>O1CCCC1.[Ni]>[O:11]1[C:12]2[C:4]([NH2:1])=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 128059492,3-Dihydro-7-nitrobenzofuranHCID 178418361HCID 178418361, compound

Product 1

HCID 128059502,3-Dihydro-1-benzofuran-7-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

39.4 g of 2,3-dihydro-7-nitrobenzofuran (prepared by the method described in Journal of Heterocyclic Chemistry, vol. 5, No. 1, p. 1 (1968)) in 200 ml of tetrahydrofuran was hydrogenated in a Parr shaker (50 p.s.i.g. hydrogen pressure, Raney nickel catalyst, 3 hours, room temperature). The resulting mixture was filtered and the solvent was evaporated from the filtrate. The residue was recrystallized from ether to give 1, as a colorless solid, m.p.: 70°-72° C.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customthe solvent was evaporated from the filtrate
  3. customThe residue was recrystallized from ether
  4. customto give 1

Sources & evidence

ORD record
ord-a79c8dbe5eca475eb041554c08765875
Source dataset
uspto-grants-1981_11
Patent number
US04302592

Reaction notes

Loading…