Lithium Hydroxide → 2-Cyanoisonicotinic Acid

HRID 1397283

Reaction equation

HRID 1397283 reaction equation
[OH-].[Li+].[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][N:14]=1)[C:8]([O:10]C)=[O:9])#[N:4]>C1COCC1.O>[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][N:14]=1)[C:8]([OH:10])=[O:9])#[N:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 12132796Methyl 2-cyanopyridine-4-carboxylate

Product 1

HCID 27625132-Cyanoisonicotinic AcidYield 89.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (96 mg, 4.0 mmol) was added to a solution of methyl 2-cyanoisonicotinate (0.6 g, 3.7 mmol) in THF—H2O (20 mL, 7:3 v/v) at 0° C. The reaction mixture was allowed to warm up to room temperature and further stirred for 1 h. The reaction mixture was concentrated under reduced pressure and then diluted with water. The aqueous layer was washed with EtOAc. The pH of the aqueous layer was adjusted to ˜3 using 1.5N HCl and the organic product was extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 2-cyanoisonicotinic acid (490 mg, yield 89%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 14.11 (br s, 1H), 8.93-8.91 (dd, J=4.9 Hz, 0.8 Hz, 1H), 8.34 (d, J=0.9 Hz, 1H), 8.11-8.10 (m, 1H). MS (ESI) m/z: Calculated for C7H4N2O2: 148.03. found: 147.2 (M−H)−.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. washThe aqueous layer was washed with EtOAc
  4. extractionthe organic product was extracted with EtOAc
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dcecbd1d3e0b4f81b76838f2d5847a74
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Linked notes

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