Hi,

 Here are three references.

Bill

1.

Synthesis of N- (pentan- 3- ylidene) - 3, 4- dimethyl aniline catalyzed by acidic ionic liquids

By Hu, Zhiyan; Luo, Shuping; Xu, Danqian

From Xiandai Nongyao (2011), 10(5), 32-33, 47. | Language: Chinese, Database: CAPLUS

The reaction of pentan- 3- one with 3, 4- dimethylaniline catalyzed by acidic ionic liqs. was studied. The condensation product N- (pentan- 3- ylidene) - 3, 4- dimethyl aniline which is the important intermediate of pendimethalin was obtained with up to 92 % yield. Carboxylic acid type acidic ionic liqs. displayed excellent catalytic activity and selectivity, and could be reused for at least seven times. This new method as a green technol. has good prospects for industrial application.

2.

Green method for synthesis of schiff base compounds from ketone and aromatic amine

By Luo, Shuping; Xu, Danqian; Xu, Zhenyuan

From Faming Zhuanli Shenqing (2011), CN 102134197 A 20110727. | Language: Chinese, Database: CAPLUS

The present invention pertains to a process for a green method for the synthesis of schiff base compds. from ketones and arom. amines under the catalysis of carboxylic acid ionic liq. For example, 1- methyl- 3- carboxymethylimidazolium chloride was added to cyclohexanone in a reaction flask, then benzenamine was added to the obtained reaction mixt. under mechanic stirring. The reaction mixt. was refluxed for 10 h with const. removal of water to give N- cyclohexylideneaniline as a final product in 98 % yield. The inventive method has advantages of simple operation, high product yield, easy produc...

~

3.

A process for the preparation of pendimethalin

By Sivasankaran, K.; Rao, Sundarraja K.; Mithyantha, M. S.; Kumar, K. N. Ravi

From Indian (1998), IN 181756 A1 19980912. | Language: English, Database: CAPLUS

A pre- emergence preplanting herbicide I which is particularly effective against weeds having broad leaves (no data given) has been prepd. The process involves the condensation of 3, 4- xylidine with di- Et ketone to form Schiff's base which is then reduced to give N- substituted xylidine, which is nitrated to given N- Nitroso Pendimethalin, which is refluxed with hydrochloric acid and aminosulfonic acid to give pendimethalin. In this process the yields are good and cost of prodn. has been reduced.

Thank you so much sir :)

Greetings

Your reaction is very fast, I guess. Dissolve your amine (1eq) in the least amount in ethanol and add drop wise diethyl ketone (1eq) by shaking or stirring for 30 minutes, it will result in the formation of the sciff base

But as this reaction is in equilibrium, i need to it in reflux condenser attched to guard tube,right?

Ya, You are right Miss. Havle....Maintain the moisture free condition.

Good Luck

ok thank u all..

It will be better to use absolute alcohol for the reaction, such it absorbs the separating water.

Ok..and what if same reaction I have to do it with NaBH4   

See https://www.researchgate.net/publication/265959505_Synergism_of_Metal_and_Organocatalysis_in_Condensation_Reactions_of_Aromatic_Aldehydes_with_Anilines_Affording_Imines_Effect_of_Catalysts_on_the_Base_of_a_Supported_Cerium%28III%29_and_Proline

Article Synergism of Metal and Organocatalysis in Condensation React...

Thank u:)

It seems you are trying to do reductive amination by insitu reduction of schiff base to get secondary amine. We had done such reactions in THF. but if schiff base formation is not complete in THF, then Toluene or cyclohexane will be a solvent of choice, as it forms an azeotrop with water, which can remove water from reaction very efficiently and drive reaction to completion. Then solvent recovery and replace with THF or methanol for NaBH4 reaction can be done. All the best!

Thank you so much..