6,7-Dinitro-2,3-dihydro-1,4-benzodioxine → 7-Nitro-2,3-dihydro-1,4-benzodioxin-6-amine

HRID 1454661

반응식

HRID 1454661 반응식
[N+:1]([C:4]1[C:13]([N+:14]([O-])=O)=[CH:12][C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]>[Fe].C(O)(=O)C>[N+:1]([C:4]1[C:13]([NH2:14])=[CH:12][C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

참가 물질

4

반응물 1

HCID 35898126,7-Dinitro-2,3-dihydro-1,4-benzodioxine

생성물 1

HCID 6072087-Nitro-2,3-dihydro-1,4-benzodioxin-6-amine수율 28.4%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

실험 절차

To a mixture of 6,7-dinitro-2,3-dihydrobenzo[1,4]dioxin (Takakis, I. M.; Hadjimihalakis, P. M. J. Heterocyclic. Chem., 1991, 28, 625., 13 g, 57.8 mmol) and acetic acid (150 mL) was added iron powder (9.6 g, 172.5 mmol) at room temperature, then the mixture was refluxed for 30 min. After cooling, the mixture was filtered through a pad of Celite and the filtrate was concentrated. The residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:1 to 1:2) to afford 3.22 g (28%) of the title compound as orange solid: 1H-NMR (CDCl3) δ 7.67 (1H, s), 6.23 (1H, s), 5,85 (2H, br.s), 4.19-4.33 (4H, m).

후처리

  1. temperaturethe mixture was refluxed for 30 min
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through a pad of Celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:1 to 1:2)

출처 및 근거

ORD 기록
ord-9221c8952edc422bb7f18b8008019df9
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07479564B2

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