5-(2-Nitrophenyl)-2-furonitrile → Methyl 5-(2-nitrophenyl)furan-2-carboximidate

HRID 1855934Notes

Reaction equation

HRID 1855934 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13]([C:15]#[N:16])=[CH:12][CH:11]=1)([O-:3])=[O:2].[CH3:17][O-:18].[Na+]>CO>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13]([C:15](=[NH:16])[O:18][CH3:17])=[CH:12][CH:11]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7385205-(2-Nitrophenyl)-2-furonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 23347019Methyl 5-(2-nitrophenyl)furan-2-carboximidateYield 1,331.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-(2-nitrophenyl)-2-furonitrile (92 g, 0.43 mole) and anhydrous methanol (1000 ml) was heated to 55° and sodium methoxide (1.5 g) was added. The steam bath was removed, the solution was stirred for two hours and stored overnight at room temperature. The solution was poured into ice water (1000 ml) and stirred for one hour. The product was collected by filtration and air dried to yield 91 g (86%) of methyl 5-(2-nitrophenyl)-2-furancarboximidate. A sample was recrystallized from isopropanol, m.p. 107°-108°.

Workup

  1. temperaturewas heated to 55°
  2. customThe steam bath was removed
  3. waitstored overnight at room temperature
  4. additionThe solution was poured into ice water (1000 ml)
  5. stirringstirred for one hour
  6. filtrationThe product was collected by filtration and air
  7. customdried

Sources & evidence

ORD record
ord-9fbd6f82e9ad4ea2b7d1b5e4dc04fc10
Source dataset
uspto-grants-1980_08
Patent number
US04217286

Reaction notes

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