3-(2-Ethoxycarbonylethenyl)-2-methyl-7-nitrobenzo[b]furan → 7-Amino-3-(2-ethoxycarbonylethyl)-2-methylbenzo[b]furan

HRID 342434Notes

Reaction equation

HRID 342434 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[CH:7][C:8]1[C:9]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[C:10]=2[O:11][C:12]=1[CH3:13])=[O:5])[CH3:2]>[Pd].O1CCOCC1.C(O)C>[NH2:18][C:14]1[C:10]2[O:11][C:12]([CH3:13])=[C:8]([CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:9]=2[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 1

HCID 702015513-(2-Ethoxycarbonylethenyl)-2-methyl-7-nitrobenzo[b]furan

Product 1

HCID 702004597-Amino-3-(2-ethoxycarbonylethyl)-2-methylbenzo[b]furanYield 103.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

10%-Palladium on carbon (30 mg) was added to a solution of 3-(2-ethoxycarbonylethenyl)-2-methyl-7-nitrobenzo[b]furan (210 mg) in a mixture of dioxane (3 ml) and ethanol (1 ml). The mixture was hydrogenated at 3 atoms for 3 hours and the catalyst was filtered off. The filtrate was concentrated in vacuo to give 7-amino-3-(2-ethoxycarbonylethyl)-2-methylbenzo[b]furan (195 mg).

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-69b99deec2b449e7944ffbabee995c54
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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