Ethanol → HCID 68154234, compound

HRID 1019434Notes

Reaction equation

HRID 1019434 reaction equation
O[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:12]=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.C([OH:24])C>>[OH:24][C:16]1[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=1[N:14]=[CH:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 7813p-ToluidineHCID 128192-Hydroxy-1-naphthaldehyde

Product 1

HCID 68154234HCID 68154234, compound

Conditions

Temperature
70 °C

Procedure

3.44 g (20.0 mmol) of 2-hydroxy-1-naphthaldehyde was dissolved in 50 ml ethanol under heating, and 2.14 g (20.0 mmol) of p-toluidine was added. After stirring under reflux at 70° C. for 1 hour, completion of the reaction was confirmed by TLC. Upon concentration of the solution with an evaporator to about 40 ml, a crystal was formed, which was filtered by Kiriyama funnel. Drying under reduced pressure at 25° C. for 24 hours gave 2-hydroxy-1-naphthylmethylidene-4-methylaniline (hereinafter, also referred to as “HNPT”) as a yellow crystal (4.70 g, 90%). 1.06 g (4.00 mmol) of HNPT was dissolved in a mixed solvent of 20 ml tetrahydrofuran and 30 ml ethanol, and 50 ml of an ethanol solution of 0.40 g (2.00 mmol) of copper acetate monohydrate was added with stirring. Upon stirring under reflux at 70° C. for 1 hour, a crystal was deposited. Completion of the reaction was confirmed by TLC. The resulting crystal was filtered by Kiriyama funnel, and washed sufficiently with ethanol. Drying under reduced pressure at 25° C. for 24 hours gave a crude product of a complex compound NPTCu of the following formula as a red-brown crystal (1.17 g, 94%). A part of the resulting crystal was dissolved in tetrahydrofuran, and ethanol having a 4-fold volume thereof was added to deposit a crystal. This crystal was filtered, and dried under reduced pressure to give a purified product of the complex compound NPTCu.

Workup

  1. temperatureunder heating
  2. customUpon concentration of the solution with an evaporator to about 40 ml
  3. customa crystal was formed
  4. filtrationwhich was filtered by Kiriyama funnel
  5. customDrying under reduced pressure at 25° C. for 24 hours

Sources & evidence

ORD record
ord-c944be71b589410ea49d2bec97098f9d
Source dataset
uspto-grants-2014_05
Patent number
US08715523B2

Reaction notes

Loading…