5-Nitrofurfural → HCID 20183842, compound

HRID 255644Notes

Reaction equation

HRID 255644 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:10]=[C:11]([C:15](=[O:17])[CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.[N+:25]([C:28]1[O:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)([O-:27])=[O:26]>C(O)C>[F:24][C:21]1[CH:20]=[CH:19][C:18]([N:9]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([N:1]=[CH:32][C:31]4[O:34][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=4)=[CH:7][CH:6]=3)=[CH:16][C:15](=[O:17])[C:11]([C:12]([OH:14])=[O:13])=[CH:10]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 127745-NitrofurfuralHCID 15591126HCID 15591126, compound

Product 1

HCID 20183842HCID 20183842, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 10 ml of ethanol were suspended 0.3 g of 6-(4-aminophenyl)-1-(4-fluorophenyl)-4-oxo-1,4-dihydronicotinic acid and 0.15 g of 5-nitrofurfural, and the suspension was subjected to reaction at 80° C. for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and the insolubles were removed by filtration. The solvent was removed by distillation under reduced pressure. Then, 10 ml of diethyl ether was added to the residue, and the insolubles were collected by filtration to obtain 0.13 g of 1-(4-fluorophenyl)-6-[4-{(5-nitrofurfurylidene)amino}-phenyl]-4-oxo-1,4-dihydronicotinic acid having a melting point of 129°-131° C.

Workup

  1. customthe suspension was subjected to reaction at 80° C. for 2 hours
  2. customAfter completion of the reaction
  3. customthe insolubles were removed by filtration
  4. customThe solvent was removed by distillation under reduced pressure
  5. additionThen, 10 ml of diethyl ether was added to the residue
  6. filtrationthe insolubles were collected by filtration

Sources & evidence

ORD record
ord-48445063fa804a3faa8920e6d5984b15
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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