Benzaldehyde → 3-Nitro-6-styrylbenzamide

HRID 968351Notes

Reaction equation

HRID 968351 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH3:12])#[N:2].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-:22].[K+].[K+]>CO>[N+:9]([C:7]1[CH:8]=[C:3]([C:4]([CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:6]=1)[C:1]([NH2:2])=[O:22])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 11430Potassium CarbonateHCID 3501432-Methyl-5-nitrobenzonitrile

Product 1

HCID 544940833-Nitro-6-styrylbenzamideYield 785.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-cyano-4-nitrotoluene (10 g, 6.17 mmol), benzaldehyde (6.51 g, 6.17 mmol) and potassium carbonate (20 g) in MeOH (200 mL) was heated at reflux for 10 min. The mixture was cooled to ambient temperature over 30 min, whereupon precipitation of the product was complete. The product was isolated by filtration and washed successively with 1N HCl, water and MeOH then air dried. There was obtained 13.0 g of the benzamide (mp 269.8° C.) as evident from the lack of a nitrile adsorption in the IR and the appearance of peaks at 3357.1, 3193.6 (—NH2) and 1648.7 cm−1 (H2NC(═O)—); LRMS (M−NO)+ m/z=238.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 min
  3. customThe product was isolated by filtration
  4. washwashed successively with 1N HCl, water and MeOH
  5. customair dried

Sources & evidence

ORD record
ord-1c411ba6f7b549718d0093f63231fa9e
Source dataset
uspto-grants-2005_10
Patent number
US06958356B2

Reaction notes

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