Reduction of N-Cinnamylidene-

m-Nitroaniline
Reduction of N-Cinnamylidene-m-Nitroaniline
Reduction electron transfer
processes
Ions/neutral atoms gain
electrons

Double and triple bonds add
hydrogen across the -bond

Carbon forms covalent bonds and
doesnt really gain electrons

Involve increase in electron density
around carbon
Removal of an electronegative
atom
Reduction of N-Cinnamylidene-m-Nitroaniline
Reduction by metal hydrides
Different metal hydrides have different reactivities toward different functional groups
specific towards certain functional group while leaving others intact

Lithium Aluminum Hydride (LiAlH
4
)
Very reactive
Reduces aldehydes, ketones, esters

Sodium Borohydride (NaBH
4
)
Less reactive than previous
Reduces aldehydes and ketones
DOES NOT REDUCE ESTERS



Reduction of N-Cinnamylidene-m-Nitroaniline
Imines are formed by the condensation of a 1 amine with an aldehyde or ketone





Imines can add one mole of H
2
with a catalyst (nickel, palladium, platinum) to make 2 amine
Catalytic hydrogenation reduces C=C, CC, N=O, AND C-X

Use of sodium borohydride will eliminate problem

Reduction of N-Cinnamylidene-m-Nitroaniline
Reaction
Reduction of N-Cinnamylidene-m-Nitroaniline
Mechanism Reductive Amination mechanism
Reduction of N-Cinnamylidene-m-Nitroaniline
Mechanism cont.
Procedure
1. Place 0.6 g of cinnamaldehyde, 0.6 g of m-nitroaniline, and 5 mL of
cyclohexane in a round bottom flask
2. Set up for simple distillation
3. Distill until ~4 mL of cyclohexane has been collected in the receiving flask
(Stop heating when the distillation rate decreases)
4. Add 5 mL of cyclohexane and resume distillation (Stop heating when the
distillation rate decreases)
5. Remove from heat source
6. Add 4 mL of methanol to the stillpot and set up for reflux
7. Mix 0.15 g sodium borohydride in 3 mL of methanol (Sodium
borohydride reacts slowly with methanol. PREPARE THIS SOLUTION IN
AN UNSTOPPERED FLASK AND IMMEDIATELY BEFORE USE DO NOT
PREPARE UNTIL YOU ARE READY FOR THIS SOLUTION)
8. Add the sodium borohydride solution through the top of the reflux
condensor (Try to add the solution directly to imine solution without
touching the walls of the condensor within 1 minute)

Procedure
9. Reflux the rxn. Mixture for 15 min.
10. Cool the mixture to RT and add 10 mL of water
11. Stir the solution for 10-15 min.
12. Collect the crystals by vacuum filtration and wash them with water.
13. Weigh the product to determine percent yield, find the mp
14. Perform the qualitative test for unsaturation using the bromine in
dichloromethane and record the results