4-Chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran-3-one → 7-Amino-4-chloro-2,3-dihydro-2,2-dimethylbenzofuran-3-one

HRID 440658Notes

Reaction equation

HRID 440658 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([N+:14]([O-])=O)=[CH:4][CH:3]=1>C(O)(=O)C.O.[Fe]>[NH2:14][C:5]1[C:6]2[O:10][C:9]([CH3:11])([CH3:12])[C:8](=[O:13])[C:7]=2[C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 1

HCID 224048104-Chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran-3-one

Product 1

HCID 224047237-Amino-4-chloro-2,3-dihydro-2,2-dimethylbenzofuran-3-oneYield 76.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

By the method of Example 1, Step E, 4.82 g (0.020 mole) of 4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran-3-one and 5.0 g of powdered iron were reacted in 80 mL of glacial acetic acid and 10 mL of water, yielding 3.25 g of 7-amino-4-chloro-2,3-dihydro-2,2-dimethylbenzofuran-3-one as an oil which subsequently solidified, m.p. 71°-73° C.

Sources & evidence

ORD record
ord-71af8db5ec0c423787fce94d7cbcbc97
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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