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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1695582Generated: October 27, 2026

4-Methoxy-benzofuran-3-one oxime → 4-Methoxy-2,3-dihydrobenzofuran-3-amine

https://huagongshe.com/reaction/1695582

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Methoxy-benzofuran-3-one oximeHCID 86634184—
ReactantHCID 178418361HCID 178418361—
CatalystNickelHCID 935—
SolventMethanolHCID 887—
SolventTetrahydrofuranHCID 8028—
Product4-Methoxy-2,3-dihydrobenzofuran-3-amineHCID 6721252298%

Reaction Steps

A mixture of the above described 4-methoxy-benzofuran-3-one oxime (27.7 g, 155 mmol; HPLC 1.448 min) and Raney-Nickel (13.85 g) in tetrahydrofuran (700 mL) and methanol (700 mL) was hydrogenated at 100 bar hydrogen-pressure at 100° C. for 22 h. Filtered the catalyst off, washed with methanol and tetrahydrofuran, all volatiles very removed in vacuum to give the title compound as a brown oil (24.7 g, 98%, HPLC 0.4 min), MS (ISP) m/e=166.2 [(M+H)+].

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08163740B2
Source datasetuspto-grants-2012_04
ORD IDord-bb91425f258046d6abd6dc73002dcc6a
Source noteuspto-grants-2012_04