p-Toluenesulfonic acid → 3-hydroxy-N'-(1-methylethylidene)-2-naphthohydrazide

HRID 844394Notes

Reaction equation

HRID 844394 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.[C:16]1(C)[CH:21]=CC(S(O)(=O)=O)=C[CH:17]=1>CC(C)=O>[OH:1][C:2]1[C:3]([C:12]([NH:14][N:15]=[C:16]([CH3:21])[CH3:17])=[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 6101p-Toluenesulfonic acidHCID 726993-Hydroxy-2-naphthoic acid hydrazide

Product 1

HCID 45219753-hydroxy-N'-(1-methylethylidene)-2-naphthohydrazide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

A four neck flask (3 liters) equipped with a thermometer, a reflux condenser and a stirrer was charged with 121.2 g (0.6 mol) of 3-hydroxy-2-naphthohydrazide, 1.14 g (0.006 mol) of p-toluenesulfonic acid and 2 liters of acetone and then heated under reflux for 5 hours. The reaction liquid was cooled down to 20° C. or lower, and then crystal was filtered off and dried under reduced pressure, whereby the intended compound (slightly yellow crystal) was obtained.

Workup

  1. customA four neck flask (3 liters) equipped with a thermometer, a reflux condenser and a stirrer
  2. temperatureheated
  3. temperatureunder reflux for 5 hours
  4. customThe reaction liquid
  5. filtrationlower, and then crystal was filtered off
  6. customdried under reduced pressure, whereby the intended compound (slightly yellow crystal)
  7. customwas obtained

Sources & evidence

ORD record
ord-5d6f44b48cc54f7980cfe0dbf05aba55
Source dataset
uspto-grants-2002_04
Patent number
US06380288B1

Reaction notes

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