6-Butyl-2-oxo-1,2-dihydro-isonicotinic acid → 6-Butylpyridin-2-ol

HRID 1656319Notes

Reaction equation

HRID 1656319 reaction equation
[CH2:1]([C:5]1[NH:6][C:7](=[O:14])[CH:8]=[C:9]([CH:13]=1)C(O)=O)[CH2:2][CH2:3][CH3:4]>N1C2C(=CC=CC=2)C=CC=1.[Cu-]=O>[CH2:1]([C:5]1[NH:6][C:7](=[O:14])[CH:8]=[CH:9][CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 540903426-Butyl-2-oxo-1,2-dihydro-isonicotinic acid

Product 1

HCID 233521006-Butylpyridin-2-ol

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 7047QuinolineSolvent

Procedure

4.9 g (25 mmol) of 6-butyl-2-oxo-1,2-dihydro-isonicotinic acid are refluxed for 1.5 h with 1.79 g (12.5 mmol) of copper(I) oxide in 50 ml of quinoline (237° C). After filtering off, the volatile constituents are removed by distillation in vacuo (110° C. at 17 mbar, then 67° C. at 9 mbar). The residue is chromatographed twice on silica gel using dichloromethane/methanol (40:1) → (20:1) and the product is stirred in petroleum ether.

Workup

  1. filtrationAfter filtering off
  2. customthe volatile constituents are removed by distillation in vacuo (110° C. at 17 mbar
  3. custom67° C.
  4. customThe residue is chromatographed twice on silica gel

Sources & evidence

ORD record
ord-d0d9d8fc1bf949f39bf4581fb26aef57
Source dataset
uspto-grants-1993_10
Patent number
US05254543

Reaction notes

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