Dimethylformamide → Methyl 2-cyano-6-methoxyisonicotinate

HRID 571869Notes

Reaction equation

HRID 571869 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:14][N:15](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:14]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:15]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 13339618Methyl 2-chloro-6-methoxyisonicotinate

Product 1

HCID 11252506Methyl 2-cyano-6-methoxyisonicotinate

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
160 °C

Procedure

Under N2, methyl 2-chloro-6-methoxyisonicotinate (CAS 42521-10-8) (3.97 g, 19.7 mmol, Eq: 1.00), zinc cyanide (2.77 g, 23.6 mmol, Eq: 1.2) and Tetrakis-triphenylphosphin-palladium (1.14 g, 985 μmol, Eq: 0.05) were mixed in DMF (67.5 ml). The RM was stirred under microwave at 160° C. for 30 minutes. Control with LC-MS: the reaction was finished.

Sources & evidence

ORD record
ord-99f0653e292a4eeab516486adb003f18
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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