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

HRID 52462

반응식

HRID 52462 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 10313229titanium(III) trichloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8bb1305d46414b1fb4b3af0acb2da657
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616586

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