Acetic Acid → Acetamide, N-[10-(1,3-benzodioxol-5-yl)-7,9-dihydro-7,9-dioxo-8H-1,3-benzodioxolo[4,5-f]isoindol-8-yl]-

HRID 2354599노트

반응식

HRID 2354599 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]4[C:25](=[O:26])[O:24][C:23](=O)[C:12]=4[CH:13]=[C:14]4[C:22]=3[C:18]3[O:19][CH2:20][O:21][C:17]=3[CH:16]=[CH:15]4)=[CH:9][C:4]=2[O:3][CH2:2]1.O.[NH2:29][NH2:30].[C:31]([OH:34])(=O)[CH3:32]>>[O:21]1[C:17]2[CH:16]=[CH:15][C:14]([C:13]3[C:9]4[C:8](=[CH:7][CH:6]=[C:5]5[O:1][CH2:2][O:3][C:4]5=4)[CH:10]=[C:11]4[C:25](=[O:26])[N:29]([NH:30][C:31](=[O:34])[CH3:32])[C:23](=[O:24])[C:12]=34)=[CH:22][C:18]=2[O:19][CH2:20]1

참가 물질

4

반응물 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 527377710-Benzo[1,3]dioxol-5-yl-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxole-7,9-dione

생성물 1

HCID 5273798Acetamide, N-[10-(1,3-benzodioxol-5-yl)-7,9-dihydro-7,9-dioxo-8H-1,3-benzodioxolo[4,5-f]isoindol-8-yl]-수율 86%

실험 절차

A solution of anhydride 1 (145 mg, 0.4 mmol) in glacial acetic acid (10 mL) was refluxed with hydrazine hydrate (0.023 mL, 0.48 mmol) for 24 h under nitrogen and then poured, after cooling, into ice water. The resulting precipitate was filtered and dried under reduced pressure. The residue was purified by column chromatography on silica gel using CH2Cl2/MeOH (30:1 to 20:1, v/v) to give 25 (143 mg, 86%) as a yellow solid. mp 281-283° C.; 1H NMR (CDCl3) δ 8.34 (s, 1H, H4), 7.69 (d, 1H, H5, J=8.7 Hz), 7.46 (s, 1H, NHAc), 7.38 (d, 1H, H6, J=8.7 Hz), 6.84-6.87 (m, 3H, H2′+H5′+H6′), 6.06 (AB, 2H, 3′,4′-OCH2O—, Δδ=16.5 Hz, J=1.5 Hz), 5.98 (AB, 2H, 7,8-OCH2O—, Δδ=5.4 Hz, J=1.2 Hz), 2.17 (s, 3H, NHCOCH3); MS (EI) m/z 418 [M]+.

후처리

  1. additionpoured
  2. filtrationThe resulting precipitate was filtered
  3. customdried under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-9982b5b4fa1d45f6b2d0c2467f1f04fb
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754718B2

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