Ammonia → Isonicotinaldehyde 1-oxide

HRID 615139Notes

Reaction equation

HRID 615139 reaction equation
[C:1]([O:7]CC)(=O)[CH2:2][C:3]([CH3:5])=O.N.C(OC(C1C(C2C=C[N+:25]([O-:28])=[CH:24][CH:23]=2)C(C(OCC)=O)=C(C)NC=1C)=O)C>C(O)C>[N+:25]1([O-:28])[CH:5]=[CH:3][C:2]([CH:1]=[O:7])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8868Ethyl AcetoacetateHCID 105215042,6-Dimethyl-4-(1-oxido-4-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

Product 1

HCID 81636Isonicotinaldehyde 1-oxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Analogously to the process described in Example 1 there is obtained from 12.3 g of pyridine-4-carboxaldehyde-1-oxide, 25.7 ml of ethyl acetoacetate and 10 ml of 30% aqueous ammonia in 20 ml of absolute ethanol, 2,6-dimethyl-4-(1-oxido-4-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester which, after recrystallisation from 100 ml of isopropanol, melts at 229°-231°.

Sources & evidence

ORD record
ord-8ba03d87279443249f4588b8c69f280d
Source dataset
uspto-grants-1985_02
Patent number
US04497808

Reaction notes

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