Furfural → 3-hydroxy-N'-(2-furylmethylene)-2-naphthohydrazide

HRID 844397Notes

Reaction equation

HRID 844397 reaction equation
[OH:1][C:2]1[C:3]([C:12]([NH:14][NH2:15])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:16](=O)[C:17]1[O:21][CH:20]=[CH:19][CH:18]=1>CO>[OH:1][C:2]1[C:3]([C:12]([NH:14][N:15]=[CH:16][C:17]2[O:21][CH:20]=[CH:19][CH:18]=2)=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 7362FurfuralHCID 726993-Hydroxy-2-naphthoic acid hydrazide

Product 1

HCID 9586453-hydroxy-N'-(2-furylmethylene)-2-naphthohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A four neck flask (2 liters) equipped with a thermometer, a reflux condenser and a stirrer was charged with 101 g (0.5 mol) of 3-hydroxy-2-naphthohydrazide and 1.5 liter of methanol, and 57.6 g (0.6 mol) of furfural was dropwise added thereto in 30 minutes while stirring at room temperature. After heating under reflux for 5 hours, the reaction liquid was cooled down to 20° C. or lower, and crystal was filtered off. The crystal was washed with a small amount of methanol and then dried under reduced pressure, whereby the intended compound (slightly yellow crystal) was obtained.

Workup

  1. customA four neck flask (2 liters) equipped with a thermometer, a reflux condenser and a stirrer
  2. additionwas dropwise added
  3. temperatureAfter heating
  4. temperatureunder reflux for 5 hours
  5. customthe reaction liquid
  6. temperaturewas cooled down to 20° C.
  7. filtrationlower, and crystal was filtered off
  8. washThe crystal was washed with a small amount of methanol
  9. customdried under reduced pressure, whereby the intended compound (slightly yellow crystal)
  10. customwas obtained

Sources & evidence

ORD record
ord-12e4b6b35d04445c894f134bfd5a6d93
Source dataset
uspto-grants-2002_04
Patent number
US06380288B1

Reaction notes

Loading…