Ammonium Chloride → 5-Bromobenzofuran-7-amine

HRID 1162082노트

반응식

HRID 1162082 반응식
[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

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 53402950HCID 53402950, 화합물

생성물 1

HCID 587718835-Bromobenzofuran-7-amine

시약·촉매·용매 2

HCID 23925Iron촉매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-44c4ed1695744a70bddbfb5ed2cc34a2
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820675B2

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