Acetic Acid → 8-Bromo-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

HRID 52462

反応式

HRID 52462 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-])=O)[CH:10]=1)[N:7]([C:14]([C:16]([O:18]CC)=O)=[O:15])[CH2:6][CH2:5]2.O.C(O)(=O)C>C1COCC1.[Cl-].[Cl-].[Cl-].[Ti+3]>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:5][CH2:6][N:7]3[C:14](=[O:15])[C:16](=[O:18])[NH:11][C:9]([CH:10]=1)=[C:8]23

参加物

6

反応物 3

HCID 176Acetic AcidHCID 962WaterHCID 100202975-bromo-7-nitro-N-ethoxalylindoline

生成物 1

HCID 117777348-Bromo-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione収率 50%

試薬・触媒・溶媒 2

HCID 10313229titanium(III) trichloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-bromo-7-nitro-N-ethoxalylindoline (2.0 g, 5.83 mmol) in a mixture of THF (50 mL), water (10 mL), and acetic acid (10 mL) was added aqueous 20% titanium trichloride (31 mL, 40.8 mmol) and the mixture was stirred for 4 h at room temperature. The precipitates formed were collected by filtration, washed with diluted aqueous hydrochloric acid and then distilled water, and dried in vacuo to give 772 mg of the title compound (50%): mp>300° C.; 1H NMR (270 MHz, DMSO-d6) δ11.91 (bs, 1H), 7.21 (d, 1H, J=1 Hz), 7.02 (d, 1H, J=1 Hz), 4.22 (t, 2H, J=7 Hz), 3.32 (t, 2H, J=7 Hz).

後処理

  1. customThe precipitates formed
  2. filtrationwere collected by filtration
  3. washwashed with diluted aqueous hydrochloric acid
  4. dry with materialdistilled water, and dried in vacuo

出典と根拠

ORDレコード
ord-8bb1305d46414b1fb4b3af0acb2da657
出典データセット
uspto-grants-1997_04
特許番号
US05616586

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