5,6-Dinitro-1,3-benzodioxole → 6-Nitro-1,3-benzodioxol-5-amine

HRID 577612

反応式

HRID 577612 の反応式
[N+:1]([C:4]1[C:12]([N+:13]([O-])=O)=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]>C(O)(=O)C>[N+:1]([C:4]1[C:12]([NH2:13])=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

参加物

3

反応物 1

HCID 6113255,6-Dinitro-1,3-benzodioxole

生成物 1

HCID 6026656-Nitro-1,3-benzodioxol-5-amine収率 84.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

Compound 5,6-dinitrobenzo[d][1,3]dioxole (6.0 g, 28.3 mmol) was added to stirred glacial acetic acid (120 mL) under N2 atmosphere. After the mixture was heated to boiling, the heat source was removed and iron powder (4.75 g) added with vigorous stirring. Quick spontaneous boiling occurred, the mixture turned dark and the exothermic reaction subsided (2-5 min). The mixture was refluxed for 10 min and poured into ice/water. The orange-red product was isolated by filtration, dissolved in glacial acetic acid, and the solution filtered while hot. The filtrate was poured into ice-cold water. The orange-red solid product was isolated by filtration and dried to provide compound 6-nitrobenzo[d][1,3]dioxol-5-amine (4.35 g, 84%). LCMS: 183 [M+1]+; 1H NMR (DMSO-d6) δ 6.06 (s, 2H), 6.51 (s, 1H), 7.36 (s, 1H), 7.73 (s, 2H).

後処理

  1. temperatureAfter the mixture was heated
  2. customthe heat source was removed
  3. additioniron powder (4.75 g) added with vigorous stirring
  4. customthe exothermic reaction
  5. custom(2-5 min)
  6. temperatureThe mixture was refluxed for 10 min
  7. customThe orange-red product was isolated by filtration
  8. filtrationthe solution filtered while hot
  9. additionThe filtrate was poured into ice-cold water
  10. customThe orange-red solid product was isolated by filtration
  11. customdried

出典と根拠

ORDレコード
ord-6e6029a8c7c24decb7ed0e385748c29e
出典データセット
uspto-grants-2015_05
特許番号
US09040556B2

関連ノート

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