5-(4-Nitrophenyl)-1,3-oxazole → 4-(1,3-Oxazol-5-yl)aniline

HRID 28583

反応式

HRID 28583 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][CH:13]=[N:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.CO.[Fe]>[O:14]1[C:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)=[CH:11][N:12]=[CH:13]1

参加物

5

反応物 1

HCID 27370685-(4-Nitrophenyl)-1,3-oxazole

生成物 1

HCID 5177474-(1,3-Oxazol-5-yl)aniline収率 83.2%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

A mixture of 5-(4-nitro-phenyl)-oxazole (2.0 g, 10.5 mmol), iron powder (2.4 g, 42.8 mmol) in acetic acid (5 ml) and methanol (30 ml) was stirred at 60° C. for 1 hour. After filtration through a pad of celite under suction, the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (3:4 followed by 3:2) to give 4-oxazol-5-yl-phenyl-amine (1.4 g, 83% yield). 1H NMR (acetone-d6) δ 5.0 (br s, 2H, NH), 6.76 (d, 2H, J=8.7 Hz, Ar), 7.12 (s, 1H, Ar), 7.45 (d, 2H, J=8.6 Hz, Ar), 8.04 (s, 1H, Ar).

後処理

  1. filtrationAfter filtration through a pad of celite under suction
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography
  4. washeluting with ethyl acetate-hexane (3:4 followed by 3:2)

出典と根拠

ORDレコード
ord-6f1e12607b364e42a2848d5e70461bf3
出典データセット
uspto-grants-2008_09
特許番号
US07419984B2

関連ノート

読み込み中…