Hydrochloric Acid → 2-Cyano-6-methylisonicotinic acid

HRID 571873Notes

Reaction equation

HRID 571873 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[N:12]=1)[C:6]([O:8]C)=[O:7])#[N:2].[Li+].[OH-].Cl>O1CCCC1.CO.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[N:12]=1)[C:6]([OH:8])=[O:7])#[N:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58802283Methyl 2-cyano-6-methylisonicotinate

Product 1

HCID 722157192-Cyano-6-methylisonicotinic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under N2, methyl 2-cyano-6-methylisonicotinate (0.490 g, 2.78 mmol, Eq: 1.00) was dissolved in Tetrahydrofuran (25 ml) and Methanol (3.03 ml). At 0° C., 1M LiOH in H2O (3.48 ml, 3.48 mmol, Eq: 1.25) was added and the RM was stirred at 0° C. for 30 minutes. Control with TLC: the reaction was finished. The reaction mixture was acidified with 1M HCl. The mixture was diluted with H2O and extracted with EtOAc. The organic phase was dried over MgSO4; filtered; concentrated in vacuo. Pink solid. MS (EIC): 160.8 ([M+H]+)

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86892c5b6fd143b382326cb06d19468c
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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