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

HRID 28583

반응식

HRID 28583 반응식
[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

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6f1e12607b364e42a2848d5e70461bf3
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

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