Acetic Anhydride → Nicotinamide

HRID 1659216Notes

Reaction equation

HRID 1659216 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-bb51612981fa4463b953d499474acddf
Source dataset
uspto-grants-1981_12
Patent number
USRE030811

Reaction notes

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