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

HRID 1439384Notes

Reaction equation

HRID 1439384 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 2 hours and stored overnight at room temperature. The solution was poured into ice water (1000 ml) and stirred for 1 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 1 hour
  6. filtrationThe product was collected by filtration and air
  7. customdried

Sources & evidence

ORD record
ord-98e04b5ed94849d48c60c80dd99c1ad5
Source dataset
uspto-grants-1977_11
Patent number
US04059597

Reaction notes

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