Dimethylformamide → Methyl 2-cyano-6-methylisonicotinate

HRID 571872

Reaction equation

HRID 571872 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][N:14](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:13]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:14]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 2759833Methyl 2-Chloro-6-methylisonicotinate

Product 1

HCID 58802283Methyl 2-cyano-6-methylisonicotinate

Reagents, catalysts & solvents 1

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

Conditions

Temperature
160 °C

Procedure

Under N2, methyl 2-chloro-6-methylisonicotinate (CAS 3998-90-1) (1.000 g, 5.39 mmol, Eq: 1.00), zinc cyanide (759 mg, 6.47 mmol, Eq: 1.2) and Tetrakis-triphenylphosphin-palladium (623 mg, 539 μmol, Eq: 0.1) were mixed in DMF (17 ml). The RM was stirred under microwave at 160° C. for 30 minutes. Control with TLC: the reaction was finished. The RM was partitioned between EtOAc and water; extracted; the organic phase was dried over MgSO4; filtered; concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 100 g, 5% to 30% EtOAc in heptane). Purple solid. MS (ISP): 177.2 ([M+H]+)

Workup

  1. customThe RM was partitioned between EtOAc and water
  2. extractionextracted
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (silica gel, 100 g, 5% to 30% EtOAc in heptane)

Sources & evidence

ORD record
ord-8aad0ea1d32840aab9b9837366dd4171
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Linked notes

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