Acetic Anhydride → Nicotinamide

HRID 461891Notes

Reaction equation

HRID 461891 reaction equation
[N+](C1C=CC=CC=1C=O)([O-])=O.C([N:14](CC)[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][C:19](C)=[N:18][CH:17]=1)C.C(OC(=O)C)(=O)C.C(N(CC)C(=O)C1C=CC(C=CC2C=CC=CC=2[N+]([O-])=O)=NC=1)C>>[C:15]([NH2:14])(=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 111012-NitrobenzaldehydeHCID 10081297N,N-diethyl-6-methylnicotinamideHCID 53931032HCID 53931032, compound

Product 1

HCID 936Nicotinamide

Procedure

Reaction of o-nitrobenzaldehyde (41.7 g., 0.276 mole) with N,N-diethyl-6-methylnicotinamide (53.1 g., 0.276 mole) in the presence of acetic anhydride (56.3 g., 0.552 mole) according to the method of L. Horwitz, J. Org. Chem., 21, 1039 (1956) provides 67.4 g. (75%) of N,N-diethyl-6-(o-nitrostyryl)-nicotinamide. Crystallization from acetonitrile affords the analytically pure nicotinamide having a melting point of 145°-147° C. (corr.).

Workup

  1. custom, 21, 1039 (1956) provides 67.4 g
  2. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-4afabe8d144a48fb86c73c869558e7b4
Source dataset
uspto-grants-1977_12
Patent number
US04064254

Reaction notes

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