Acetic Anhydride → N-(2,2-Dimethyl-2H-1-benzopyran-7-yl)acetamide

HRID 1902838노트

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HRID 1902838 반응식
[CH3:1][C:2]1([CH3:15])[O:7][C:6]2[CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=[CH:11][C:5]=2[CH:4]=[CH:3]1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>[Fe].C(O)(=O)C>[C:16]([NH:12][C:9]1[CH:10]=[CH:11][C:5]2[CH:4]=[CH:3][C:2]([CH3:15])([CH3:1])[O:7][C:6]=2[CH:8]=1)(=[O:18])[CH3:17]

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 132228872,2-Dimethyl-7-nitro-2h-1-benzopyran

생성물 1

HCID 14831889N-(2,2-Dimethyl-2H-1-benzopyran-7-yl)acetamide

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

반응 조건

온도
120 °C

실험 절차

2,2-Dimethyl-7-nitro-2H-benzo[b]pyran (40.00 g, the preparation of which was disclosed in U.K. Pat. No. 1,548,222), glacial acetic acid (200 ml), acetic anhydride (120 ml) and electrolytic iron powder (88 g) were stirred and heated at 120° C. for 16 hours. Dilution with water, extraction via chloroform, followed by washing of the organic layer with water and sodium bicarbonate solution, drying evaporation etc., gave a crude gum which was chromatographed on a silica gel column using ethyl acetate--60°--80° petroleum ether mixtures in a gradient elution technique. Fractions homogeneous by TLC were combined and recrystallised from 60°-80° petroleum ether to give 7-acetamido-2,2-dimethyl-2H-benzo[b]pyran (5.27 g) as white needles of mp 80°-81° C.; nmr (CDCl3) δ 1.39 (6H), 2.12 (3H), 5.48 (1H, d, J=10), 6.21 (1H, d, J=10), 6.76-7.34 (3H, m), 8.95 (1H). Anal. Calcd for C13H15NO2 ; C, 71.87; H, 6.96; N, 6.45. Found: C, 72.00; H, 7.11; N, 6.23%.

후처리

  1. extractionDilution with water, extraction via chloroform
  2. washby washing of the organic layer with water and sodium bicarbonate solution
  3. customdrying
  4. customevaporation etc.
  5. customgave a crude gum which
  6. customwas chromatographed on a silica gel column
  7. customethyl acetate--60°--80° petroleum ether
  8. washmixtures in a gradient elution technique
  9. customrecrystallised from 60°-80° petroleum ether

출처 및 근거

ORD 기록
ord-2f77e639d3564941be095a6ffe27744b
출처 데이터셋
uspto-grants-1982_12
특허 번호
US04366163

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