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 2354599ノート

反応式

HRID 2354599 の反応式
[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

参加物

4

反応物 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

生成物 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]-収率 86%

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-9982b5b4fa1d45f6b2d0c2467f1f04fb
出典データセット
uspto-grants-2010_07
特許番号
US07754718B2

反応ノート

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