Acetic Anhydride → N-[2-hydroxy-5-(trifluoromethyl)phenyl]acetamide

HRID 270059

反応式

HRID 270059 の反応式
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[OH:14])([O-])=O.[C:15](OC(=O)C)(=[O:17])[CH3:16]>[Pd].CO>[OH:14][C:5]1[CH:6]=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:4]=1[NH:1][C:15](=[O:17])[CH3:16]

参加物

5

反応物 2

HCID 7918Acetic AnhydrideHCID 98162-Nitro-4-(trifluoromethyl)phenol

生成物 1

HCID 68965568N-[2-hydroxy-5-(trifluoromethyl)phenyl]acetamide収率 100.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A mixture of 2-nitro-4-(trifluoromethyl)phenol (310 mg, 1.5 mmol), palladium on carbon (10%, 125 mg) and acetic anhydride (306.3 mg, 3.0 mmol) in methanol was hydrogenated for 2 h at atmospheric pressure. The catalyst was filtered off, the filtrate was concentrated in vacuo to give crude N-[2-hydroxy-5-(trifluoromethyl)phenyl]acetamide (331 mg). A part (219.16 mg, 1.0 mmol) of N-[2-hydroxy-5-(trifluoromethyl)phenyl]acetamide was treated with [(2S)-2-methyloxiran-2-yl]methyl3-nitrobenzenesulfonate (273.27 mg, 1.0 mmol) in the presence of Cs2CO3 (406.25 mg, 1.25 mmol) in DMF (5 mL) at room temperature for 5 h. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered, concentrated. The residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum ether) to give the subtitled compound (230 mg).

後処理

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-60a3a0bdc2144fcfaf95c0dd7b8ebdb1
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

関連ノート

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