Hydrochloric Acid → 2-Cyano-6-methoxyisonicotinic acid

HRID 571870Notes

Reaction equation

HRID 571870 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH3:14])[N:12]=1)[C:6]([O:8]C)=[O:7])#[N:2].[Li+].[OH-].Cl>C1COCC1.CO.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH3:14])[N:12]=1)[C:6]([OH:8])=[O:7])#[N:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11252506Methyl 2-cyano-6-methoxyisonicotinate

Product 1

HCID 722157132-Cyano-6-methoxyisonicotinic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under N2, methyl 2-cyano-6-methoxyisonicotinate (0.433 g, 2.25 mmol, Eq: 1.00) was dissolved in THF (25.0 ml) and Methanol (3.03 ml). At 0° C., 1M LiOH in H2O (2.82 ml, 2.82 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. Light yellow solid. MS (EIC): 176.8 ([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-ea32d41a734d49979f66580d7c8df06d
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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