Hydrochloric Acid → HCID 67325241, compound

HRID 1397211Notes

Reaction equation

HRID 1397211 reaction equation
[Li+].[OH-:2].[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([CH:14]=1)C(OC)=O)#[N:4].Cl.[CH2:16]1COCC1.[OH2:21]>>[C:3]([C:5]1([CH:14]=[CH:9][CH:8]=[N:7][CH2:6]1)[C:16]([OH:21])=[O:2])#[N:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 13623673Methyl 5-cyanopyridine-3-carboxylateHCID 21881883Oxolane--water (1/1)

Product 1

HCID 67325241HCID 67325241, compoundYield 78%

Procedure

LiOH (150 mg, 6.2 mmol) was added to solution of methyl 5-cyanonicotinate (1 g, 6.17 mmol) in THF—H2O (7:3 v/v, 50 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 h. THF was then removed under reduced pressure and the reaction mixture was diluted with water and washed with EtOAc. The resulting reaction mixture was acidified with 1.5N HCl to pH 3-4. The mixture was extracted with EtOAc and the organic layer was dried over anhydrous Na2SO4. Solvent was evaporated under reduced pressure to get 3-cyanonicotinic acid as an off-white solid (0.7 g, yield 78%): 1H NMR (300 MHz, DMSO-d6) δ 13.9 (br s, 1H), 9.27 (s, 1H), 9.23 (s, 2H), 8.71 (s, 1H). MS (ESI) m/z: Calculated for C7H4N2O2: 148.03. found: 147.0 (M−H)−.

Workup

  1. customTHF was then removed under reduced pressure
  2. additionthe reaction mixture was diluted with water
  3. washwashed with EtOAc
  4. customThe resulting reaction mixture
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialthe organic layer was dried over anhydrous Na2SO4
  7. customSolvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-568619a7f07f4c3999ea33c98ecd2694
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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