3-Amino-2-hydroxyacetophenone → N-(3-acetyl-2-hydroxyphenyl)-2-(benzyloxymethyl)benzofuran-5-carboxamide

HRID 1603893Notes

Reaction equation

HRID 1603893 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[O:11][C:12]2[CH:18]=[CH:17][C:16]([C:19]([OH:21])=O)=[CH:15][C:13]=2[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[C:26]=1[OH:32])=[O:24]>>[C:23]([C:25]1[C:26]([OH:32])=[C:27]([NH:31][C:19]([C:16]2[CH:17]=[CH:18][C:12]3[O:11][C:10]([CH2:9][O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:14][C:13]=3[CH:15]=2)=[O:21])[CH:28]=[CH:29][CH:30]=1)(=[O:24])[CH3:22]

Participants

3

Reactant 2

HCID 4592943-Amino-2-hydroxyacetophenoneHCID 196063212-(Benzyloxymethyl)benzofuran-5-carboxylic acid

Product 1

HCID 19606326N-(3-acetyl-2-hydroxyphenyl)-2-(benzyloxymethyl)benzofuran-5-carboxamideYield 98%

Procedure

Following the process described in example 1 (point K), starting from 2-(benzyloxymethyl)benzofuran-5-carboxylic acid and 3-amino-2-hydroxyacetophenone, the title compound was prepared as a yellowish solid with melting point 92-94° C., which was purified by chromatography through a silica gel column (98% yield).

Workup

  1. customwas purified by chromatography through a silica gel column (98% yield)

Sources & evidence

ORD record
ord-491a49e5eb7742d1ac41bd514aea0e67
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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