2,3-Dihydro-2,2-dimethyl-7-nitrobenzofuran-3-one → 7-Amino-2,3-dihydro-2,2-dimethylbenzofuran-3-one

HRID 440661Notes

Reaction equation

HRID 440661 reaction equation
[CH3:1][C:2]1([CH3:15])[C:6](=[O:7])[C:5]2[CH:8]=[CH:9][CH:10]=[C:11]([N+:12]([O-])=O)[C:4]=2[O:3]1>C(O)(=O)C.O.[Fe]>[NH2:12][C:11]1[C:4]2[O:3][C:2]([CH3:1])([CH3:15])[C:6](=[O:7])[C:5]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 1

HCID 224047252,3-Dihydro-2,2-dimethyl-7-nitrobenzofuran-3-one

Product 1

HCID 224047467-Amino-2,3-dihydro-2,2-dimethylbenzofuran-3-oneYield 68.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

By the method of Example 1, Step E, 20.0 g (0.097 mole) of 2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran-3-one and 27.0 g (0.483 mole) of powdered iron were reacted in 85 mL of glacial acetic acid and 15 mL of water, yielding 11.79 g of 7-amino-2,3-dihydro-2,2-dimethylbenzofuran-3-one, m.p. 80°-84° C. The NMR and IR spectra of this product were consistent with the proposed structure.

Sources & evidence

ORD record
ord-942908365e9d4565bffb41e59b9b3348
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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