Ammonium Chloride → 5-Bromobenzofuran-7-amine

HRID 1162082ノート

反応式

HRID 1162082 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N+:11]([O-])=O)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[Cl-].[NH4+]>[Fe].O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 53402950HCID 53402950、化合物

生成物 1

HCID 587718835-Bromobenzofuran-7-amine

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 5-bromo-7-nitro-1-benzofuran (1.9 g, 7.9 mmol; obtained in Step 3), iron powder (2.3 g) methanol (20 mL), 1,4-dioxane (20 mL) and ammonium chloride (2.3 g dissolved in 10 mL of water), was refluxed overnight. The warm mixture was filtered through wetted Celite, which was further washed with hot methanol and the solvents were evaporated. The crude product was dissolved in hot ethanol/water (100 mL) and then water added so that product began to crystallize out. The product was collected by filtration, washed with water and dried in a vacuum oven. Yield: 1.1 g (65%). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.63 (s, 2H) 6.68 (d, J=2.0 Hz, 1H) 6.81 (d, J=2.3 Hz, 1H) 6.96 (d, J=2.0 Hz, 1H) 7.92 (d, J=2.3 Hz, 1H).

後処理

  1. temperaturewas refluxed overnight
  2. filtrationThe warm mixture was filtered through wetted Celite, which
  3. washwas further washed with hot methanol
  4. customthe solvents were evaporated
  5. dissolutionThe crude product was dissolved in hot ethanol/water (100 mL)
  6. additionwater added so that product
  7. customto crystallize out
  8. filtrationThe product was collected by filtration
  9. washwashed with water
  10. customdried in a vacuum oven

出典と根拠

ORDレコード
ord-44c4ed1695744a70bddbfb5ed2cc34a2
出典データセット
uspto-grants-2010_10
特許番号
US07820675B2

反応ノート

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