Cyanoacetamide → 5-Acetyl-2-hydroxy-6-methylnicotinonitrile

HRID 542528Notes

Reaction equation

HRID 542528 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[Na].C(OC=[CH:12][C:13]([CH2:15][C:16](=[O:18])[CH3:17])=O)C.[K+].[Br-].N1C=CC=C[C:22]1=O>CO>[C:16]([C:15]1[CH:22]=[C:3]([C:1]#[N:2])[C:4](=[O:5])[NH:6][C:13]=1[CH3:12])(=[O:18])[CH3:17]

Participants

7

Reactant 5

HCID 7898CyanoacetamideHCID 88712-PyridoneHCID 253877Potassium BromideHCID 5360545SodiumHCID 53800728HCID 53800728, compound

Product 1

HCID 27654765-Acetyl-2-hydroxy-6-methylnicotinonitrileYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

From cyanoacetamide (0.02 mol), sodium metal (0.02 g-atom) in MeOH (10 ml), and 5 (0.02 mol): 1.0 g, 28% yield; mp=233°-4° C.; NMR (DMSO-d6) δ 2.5 (s, 3H), 2.6 (s, 3H), 8.8 (s, 1H); IR (KBr), 1660 cm-1 (C=O of pyridone), 1690 cm-1 (C=O of ketone).

Sources & evidence

ORD record
ord-1cef8c10c8fa4f88a365948797e3a573
Source dataset
uspto-grants-1987_04
Patent number
US04657919

Reaction notes

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