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

HRID 858469

反応式

HRID 858469 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-36a030edc07f4afea7551484a4c2e477
出典データセット
uspto-grants-2006_12
特許番号
US07148234B2

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