Ammonium Chloride → HCID 58771883, compound

HRID 1162082Notes

Reaction equation

HRID 1162082 reaction equation
[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

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 53402950HCID 53402950, compound

Product 1

HCID 58771883HCID 58771883, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-44c4ed1695744a70bddbfb5ed2cc34a2
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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