Sodium Bicarbonate → 3,4-dihydro-1H-pyrano[4,3-c]pyridin-1-one

HRID 1844015Notes

Reaction equation

HRID 1844015 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:11]=[N:10][CH:9]=[CH:8][C:5]=1[C:6]#N.C([O-])(O)=[O:13].[Na+]>Cl>[C:6]1(=[O:13])[C:5]2[CH:8]=[CH:9][N:10]=[CH:11][C:4]=2[CH2:3][CH2:2][O:1]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 899647553-(2-Hydroxyethyl)isonicotinonitrile

Product 1

HCID 899638373,4-dihydro-1H-pyrano[4,3-c]pyridin-1-oneYield 15.29%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-(2-Hydroxyethyl) isonicotinonitrile (I-67d: 650 mg, 4.362 mmol) was heated with concentrated HCl (10 mL) at 100° C. overnight. The reaction mass was neutralized with NaHCO3 solution, extracted using DCM and the organic layer was concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 100 mg of the product (15.29% yield).

Workup

  1. extractionextracted
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customto afford the crude product
  4. customPurification by column chromatography on silica gel (1% methanol in CHCl3)

Sources & evidence

ORD record
ord-76b7e2571add47d594c900000c4ab161
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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