Tetrahydrofuran → 8-amino-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one

HRID 1727395Notes

Reaction equation

HRID 1727395 reaction equation
[N+:1]([CH:4]1[CH2:16][O:15][C:14]2[CH:13]=[CH:12][C:11]3[CH2:10][NH:9][C:8](=[O:17])[C:7]=3[C:6]=2[CH2:5]1)([O-])=O.C1COCC1.O.NN>CCO.[Ni]>[NH2:1][CH:4]1[CH2:16][O:15][C:14]2[CH:13]=[CH:12][C:11]3[CH2:10][NH:9][C:8](=[O:17])[C:7]=3[C:6]=2[CH2:5]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 575676678-nitro-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one

Product 1

HCID 575676698-amino-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-oneYield 69%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 8-nitro-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one ((69), 700 mg, 2.99 mmol) in EtOH (35 ml)/THF (5 ml) was added hydrazine monohydrate (1.65 ml, 34 mmol), followed by addition of Raney-Nickel (50 mg). The reaction mixture was stirred for 4 hr. The catalyst residue was filtered under vacuum and organic solution was concentrated in vacuo to give the title compound as a solid (420 mg, 69%). MS (ES) m/z 205.1

Workup

  1. filtrationThe catalyst residue was filtered under vacuum and organic solution
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-e20ac8f7b0d14e46932b0e1873946faa
Source dataset
uspto-grants-2009_02
Patent number
US07495111B2

Reaction notes

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